Winter Park Real Estate | Winter Park Homes and Condos for Sale

3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Investor or renovation opportunity in the Winter Park High school district! This solid block home features a great location for the buyer with vision. Opportunity awaits at 506 Lander Road in Winter Park! Situated on a spacious lot of approximately 0.22 acres, this 3-bedroom, 2-bath home offers 1,346 square feet of living space and plenty of potential for its next owner. Built in 1958, the property is ready for updates and improvements, presenting an opportunity for investors, renovators, or buyers looking to create a space of their own. The generously sized lot provides additional possibilities for outdoor living and landscaping. Conveniently located near shopping, dining, parks, and major roadways, with easy access to all that Winter Park and the surrounding areas have to offer. Bring your vision and explore the potential of this property!

506 Lander Road, Winter Park

$985,000

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

2330 Westminster Ct., Winter Park

$1,100,000

Comstock Park SubDv. ⋅ 32789 Zip Code

Exceptional opportunity to build on beautiful Bonita Drive, one of Winter Park’s most picturesque brick-lined streets, with this 0.18-acre (approximately 8,014-square-foot) homesite. Already cleared and ready for new construction, the property offers an ideal setting to create a custom residence tailored to your vision. Ideally positioned just minutes from Park Avenue’s shops and restaurants, Rollins College, the Winter Park Farmers’ Market, leading hospitals and top-rated schools, with convenient access to downtown Orlando, major roadways and area airports. Create your dream home in one of Winter Park’s most desirable residential settings.

1030 Bonita Drive, Winter Park

$620,000

3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 05 SubDv. ⋅ 32792 Zip Code

Welcome to this charming Winter Park home, featuring classic terrazzo floors and wonderful natural light. This home boasts a cozy wood-burning fireplace that serves as a focal point in the kitchen and living room, creating a warm and welcoming atmosphere. Culinary enthusiasts will delight in the kitchen's features, including an island with a breakfast bar, storage and power, elegant pendant lights, soft-close drawers and cabinets, and a stylish tile backsplash. Granite countertops and stainless-steel appliances, including a brand-new gas range, complete the culinary experience. The separate family room, with beautiful laminate flooring, offers an additional living space, perfect for relaxation or entertaining. From here, step into the enclosed lanai, where windows wrap around the entire space, offering lovely views and access to the fenced, landscaped backyard. This home also offers generous storage closets for all your needs. The primary bedroom offers a walk-in closet and ensuite bathroom with a granite counter vanity with soft-close drawers and cabinets. The remaining bedrooms share a hall bath with a dual sink granite vanity and a tub/shower combination. Located in a tremendous area, this home is just a short distance from the vibrant communities of Winter Park and Baldwin Park, and within walking distance to Winter Park High School. Other updates include a newer water heater (2024) and newer windows and doors (2020). Don't miss the opportunity to make this lovely home your own!

624 Dunraven Drive, Winter Park

$509,999

3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhouse charm with thoughtful upgrades, this home offers 1,460 square feet of inviting living space designed for both everyday comfort and entertaining. Step inside to a bright, open floor plan where the spacious living and dining areas flow effortlessly into the kitchen, complete with quartz countertops, stainless steel appliances, a built-in microwave, tile backsplash, and a window overlooking the outdoors. On the opposite side of the home, you'll find three comfortable bedrooms and two beautifully updated bathrooms, offering a practical layout with plenty of privacy. An oversized interior laundry room and enclosed porch provide additional functional space. Outside is where this home truly shines! The private backyard features a sparkling in-ground pool, a newly installed paver patio (2025), and a brand-new fence (2026), creating an inviting setting for weekend gatherings, outdoor dining, or relaxing in the Florida sunshine. Recent improvements also include a new irrigation system and control panel (2026), updated pool filtration equipment (2026), and a water heater replaced approximately three years ago. Beyond the property, enjoy a prime Winter Park location just minutes from Cady Way Trail, Winter Park Pines Golf Course, Rollins College, and the shopping, dining, and charm of Park Avenue. With its updated interiors, private pool, and convenient access to everything Winter Park has to offer, 808 Densmore Drive is ready to welcome you home!

808 Densmore Drive, Winter Park

$699,900

3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

1884 Jessica Court, Winter Park

$4,500,000

5 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

1631 Hillcrest Avenue, Winter Park

4832 Tangerine Avenue Unit 4832, Winter Park

$188,800

2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Welcome to comfortable living in desirable East Winter Park. This beautifully maintianed condominium offers a spacious and inviting floor plan in a quiet,establised community with convienent location. The resdience features generous room sizes, and a functional layout designed for comfortable everday living. The open lving room and dining areas provide a welcoming space for relaxing or entertaing, while the private screened porch offers a peaceful outdoor retreat to ejoy Florida's year-round lifestyle. Additional storage on the porch adds convienence. Community ammenities include sparkling swimming pool,clubhouse beautifully maintained grounds,and ample parking.HOA services and amentities may include exterior maintiance, landscaping,water,trash service,and roof maintenance. Buyers are encoruaged to verify all fees,services,inclusions,and commnity restrictions with the association.

4832 Tangerine Avenue Unit 4832, Winter Park

$3,195,000

4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

**OPEN HOUSE: Sunday, 10/25, 12:00–3:00 PM** | 1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms, rich in architectural elegance. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom walnut cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Thermador gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park

4786 Tangerine Avenue Unit 4786, Winter Park

$220,000

2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 square feet of living space with a spacious, functional layout designed for everyday living and entertaining. Step inside to find ceramic tile flooring, an inviting living and dining area, and a beautifully appointed kitchen featuring granite countertops, attractive cabinetry, a stylish backsplash, and stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, including a primary bedroom with a walk-in closet. Enjoy your morning coffee or unwind in the evening on the private screened-in porch overlooking a peaceful green space, complete with an additional storage closet. Interior laundry adds everyday convenience. Located in the established Wrenwood condominium community, residents enjoy access to a community swimming pool and clubhouse. The property also offers two assigned parking spaces and convenient access to major roads, shopping, restaurants, and entertainment. LOCATION, LOCATION, LOCATION! Just minutes from Full Sail University, UCF, Rollins College, Downtown Winter Park, and the popular Park Avenue shopping and dining district. Whether you're searching for your primary residence or an investment opportunity, this property offers an appealing combination of location, space, and convenience. Don't miss this opportunity to own a condominium in desirable Winter Park! Schedule your private showing today!

4786 Tangerine Avenue Unit 4786, Winter Park

$450,000

4 Beds ⋅ 3 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

Welcome to 239 Orange Terrace Drive! This charming 4 bedroom, 2.5 bath home offers 1,866 square feet of living space in a convenient Winter Park location. Situated on a spacious lot of approximately 0.21 acres with NO HOA. Step inside to discover an expansive living room filled with natural light, offering ample room for relaxing or entertaining. The adjoining formal dining room offers an inviting space for gatherings, while the kitchen features light wood cabinetry with a warm maple finish, sleek brushed nickel hardware, endless counterspace, ample storage, and a convenient pass through connecting the two spaces. Just beyond the kitchen, a separate breakfast nook offers additional dining space, along with an indoor laundry area. The home also features a distinctive brick fireplace and additional living space that can accommodate a variety of uses. With four bedrooms and two full bathrooms plus a half bath, the layout provides flexibility for guests, a home office, or everyday living. Step outside to enjoy the large backyard, offering plenty of room for outdoor activities, entertaining, or simply relaxing. A dedicated outdoor sitting area presents the perfect opportunity to create your own backyard retreat with the addition of a pergola or gazebo. Multiple storage sheds provide convenient space for tools, lawn equipment, and other outdoor essentials. With no HOA restrictions or fees, you'll enjoy added flexibility in making this property your own. Conveniently located near Lake Killarney, Park Avenue, shopping, dining, and major roadways, this property offers easy access to everything Winter Park and the surrounding Orlando area have to offer. Whether you're looking for a place to call home or an opportunity to add your personal touches, 239 Orange Terrace Drive offers space, character, and location!

239 Orange Terrace Drive, Winter Park

$695,000

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

Some homes stand out because of their finishes. Others because of their location. Rarely do you find one that brings both together so beautifully. Nestled alongside an 81-acre nature preserve, this reimagined two-story, fee-simple, end-unit townhouse offers contemporary living surrounded by nature. With approximately 1,800 square feet, 2 bedrooms, 2.5 bathrooms, and no HOA, this exceptional property feels more like a personal retreat than a traditional townhome. Designed with a modern, contemporary point of view, the home features bamboo hardwood floors and 14-foot vaulted ceilings that give the main living space an open, light-filled atmosphere, while a sleek gas fireplace brings warmth and character to the room. The kitchen includes an eat-in breakfast nook. Granite countertops, custom soft-close cabinetry, high-end stainless steel appliances, gas cooking, and a wine refrigerator combine style with everyday functionality. Additional built-ins provide attractive storage while maintaining the home's clean, cohesive aesthetic. A spacious interior laundry and utility room with an additional refrigerator provides added storage. Upstairs, the primary suite takes full advantage of the home's exceptional setting, offering peaceful views across the surrounding greenery. The primary bath features dual sinks, vanity, stone countertops, and a spacious walk-in shower with three shower heads, including a rain shower. A spacious walk-in closet completes the suite. A second bedroom and full bath provide comfortable accommodations for guests or the flexibility to create a home office or personal retreat. Parking is also a standout feature, with a one-car garage plus two designated parking spaces. Outside is where the personality of this property really comes to life. The oversized upper and lower decks create an exceptional outdoor living experience. The upper deck features a gas grill for cooking and entertaining, along with spectacular views of rocket launches from Cape Canaveral. An area provides space for relaxing, while an outdoor shower, potting station, plenty of exterior storage, and a private backyard with access to Howell Branch Creek for kayaking add to the property's distinctive appeal. Lush tropical landscaping creates a garden-like setting with citrus trees, including lemon, avocado, papaya, and a unique cocktail tree, complemented by fragrant jasmine and colorful seasonal blooms. An outdoor fire pit adds warmth and ambiance on cooler evenings. Whether you're having coffee before the day begins, sharing dinner with friends, or just enjoying the quiet after sunset, the natural surroundings make these spaces feel remarkably removed from city life. Key updates include a new tile roof replacement, HVAC installation, and water heater in 2018. Located in Winter Park's 32789 ZIP code, the home is near the Winter Park Racquet Club, Winter Park Chain of Lakes, iconic Park Avenue, fine dining, upscale boutiques, Rollins College, and highly regarded schools, including Dommerich Elementary and Winter Park High School. SunRail is also nearby, with Maitland just minutes away. Modern interiors, exceptional outdoor space with spectacular views, and the convenience of Winter Park, all in one place. For the buyer who has been waiting for something genuinely special, this may be the one.

2887 Temple Trail, Winter Park

$650,000

4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code

Virtually Staged. Set within the guard-gated community of Hawk’s Crest, this inviting single-story residence offers a beautifully maintained open floor plan with more than 1,700 square feet of comfortable living space and approximately $15,000 in luxurious recent upgrades. Fresh interior paint and neutral finishes create a bright, welcoming atmosphere, complemented by ceramic tile flooring throughout the main living areas and new carpeting in the bedrooms. At the heart of the home, the spacious kitchen features gray cabinetry, a new range and oven, stainless steel appliances, generous counter space, an expansive center island and a large pantry, opening seamlessly to the dining and living areas. The primary suite offers a spacious retreat with a walk-in closet and an en-suite bath featuring dual vanities and a walk-in shower, while additional bedrooms provide flexibility for family, guests or a home office. Sliding glass doors extend the living space to the screened lanai, enhanced with updated decking and an inviting setting for outdoor relaxation. Beyond the lanai, the fully fenced backyard, featuring newly installed fencing and landscaping, offers additional privacy and ample space for outdoor enjoyment. Residents of Hawk’s Crest enjoy resort-style amenities, including a community pool, clubhouse, fitness center, splash pad, playgrounds, dog park and private access to Lake Howell, along with the convenience of Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee at the community entrance. Ideally positioned near Winter Park’s renowned shopping, dining and everyday conveniences, this home offers an exceptional opportunity to enjoy the Hawk’s Crest lifestyle.

1458 Lone Feather Trail, Winter Park

$299,000

3 Beds ⋅ 3 Baths ⋅ Fernbrook Trails SubDv. ⋅ 32792 Zip Code

Welcome to this spacious end unit townhome in Winter Park’s Fernbrook Trails community! Featuring 3 bedrooms and 2.5 bathrooms, this home offers a convenient main floor primary bedroom and two additional bedrooms upstairs. The kitchen’s breakfast bar overlooks the family room, while a separate living and dining area provides flexible space for everyday living and entertaining. Inside laundry, a covered front porch, and a private fenced backyard complete the home. Seller willing to make upgrades. Schedule your showing today!

5468 Bracken Court, Winter Park

$4,695,000

11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park

$3,495,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

$2,629,000

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park

$479,900

3 Beds ⋅ 2 Baths ⋅ Village Green SubDv. ⋅ 32792 Zip Code

Beautifully renovated home near the end of a quiet Winter Park cul-de-sac. Luxurious tile floors run throughout, paired with all-new vinyl windows, a sliding glass door, and room-darkening cellular shades. Solid-core doors, custom closet systems, fresh paint, and knock-down ceilings complete the polished interior. The primary suite offers view of the backyard, a spacious walk-in closet with built in shelving, and an updated ensuite bathroom with a glass-enclosed rain shower. A flexible room just outside works as an office, dining space, or nursery. The kitchen features ceiling-height updated cabinetry, quartz counters and backsplash, under-cabinet and recessed lighting, and a large window to the patio. Matching black stainless Samsung appliances include a four-door fridge, dual-oven range, and Wi-Fi dishwasher, plus a deep basin sink and organized pantry storage. The kitchen opens to a spacious dining or living area with dimmable lighting and a stacked rock accent wall. Two additional bright bedrooms with large closets share a beautifully updated guest bath finished with a dual-sink vanity, floor-to-ceiling tile, and an extra-deep soaking tub behind glass doors. Outside, a wide stamped concrete driveway leads to a new modern garage door. Fresh stucco and paint frame a lush lawn. The backyard features a large covered screened patio overlooking a spacious, recently resurfaced pool with seating niches, tile, app-enabled variable-speed pump, salt-cell chlorinator, and lighting. The large yard includes new irrigation, grading, sod, a Wi-Fi timer, a six-month-old well pump, and a new vinyl fence. Major updates include PEX re-piping (2020), new sewer line (2022), roof (2019), A/C (2019/2020), updated electrical with whole-home surge protection, increased attic insulation, and a six-month-old whole-home water filtration system. Smart features cover security, cameras, Samsung washer/dryer, water heater, locks, pool equipment, and USB outlets throughout. No HOA. This home has been fully updated to a high standard. Don't miss this one!

7536 Village Green Drive, Winter Park

$305,000

3 Beds ⋅ 1 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A clean shell for a fix-and-flip or a hold-and-rent strategy, with detached ADU potential under Orange County rules. 3 bed, 1 bath, approx. 1,216 sq ft of living area on approx. 0.17 acre, FEMA Zone X (minimal flood hazard). Straightforward single-story footprint with room to improve, not expanded. Out back, a canopy of mature trees creates a shaded, private backyard sanctuary. Already handled: brand-new roof (October 2026) and a replaced water heater. Kitchen cabinets are in very good shape; if you choose to update the countertops, keep the cabinets and simply resurface and repaint. The deck is in good condition today (plan on rebuilding down the road). Still to do: central HVAC is not operational (home is cooled by window units), the shower needs a light spruce-up, and a cosmetic refresh throughout. Strong bones and a good shell for a focused remodel. Location: Lake Killarney, a 234-acre spring-fed lake, is just blocks away, where seaplanes drop in for lunch at Hillstone. Centrally located to I-4 at Fairbanks Avenue, with downtown Orlando about 15 minutes away. Less than 2 miles to the newly renovated Winter Park Village with its Regal cinema, restaurants, boutiques and patio dining, and minutes to Park Avenue, Rollins College, the Morse Museum, the Saturday Farmers Market, Trader Joe's, Whole Foods, AdventHealth Winter Park and the Winter Park SunRail station. ADU snapshot: under Orange County R-1A (Sec. 38-1426), a detached one-story ADU is typically limited to 50 percent of the primary living area or 1,000 sq ft, whichever is less, about 608 sq ft here. The lot appears to meet the 7,500 sq ft minimum. Homestead and owner-occupancy rules apply. Buyer to verify all zoning, setback, ADU eligibility, homestead and permitting items directly with Orange County Zoning. Figures are informational only and not a guarantee of approval. Renovate the primary and add a rental ADU for a two-income setup, or flip it. New roof and water heater done, interior ready for a focused remodel.

2640 Beverly Avenue, Winter Park

$1,349,000

4 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 32792 Zip Code

Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, and a convenient powder bath. The main level welcomes you with an open concept design bathed in natural light, high ceilings, and seamless flow between the living and dining areas. Perfect for culinary enthusiasts, the chef inspired kitchen is appointed with smart GE Cafe appliances, a gas range, premium quartz countertops, custom cabinetry, and a spacious center island. A private main level home office provides a quiet, dedicated environment for work or study. The first floor primary retreat offers everyday luxury with direct pool access, dual walk in closets, and a spa caliber en suite bath featuring contemporary fixtures, a dedicated linen closet, and an expansive walk in super shower. Upstairs, a versatile open loft serves as an ideal second living room, game room, or media retreat, anchoring three generous guest bedrooms with ample closet space and beautifully finished full bathrooms. Step through sliding glass doors into your private outdoor sanctuary, complete with a fully screened swimming pool featuring a sun shelf, paved patio lounging, and pre plumbing ready for your custom summer kitchen. Situated in one of Central Florida's most desirable residential pockets, this address provides premier Orange County living within comfortable walking distance to top rated Winter Park High School, Glenridge Middle School, and Brookshire Elementary. Located just minutes from the vibrant shopping, dining, and cultural attractions of Park Avenue, this turnkey 2020 build seamlessly unites contemporary luxury with quintessential Winter Park convenience.

1939 Woodcrest Drive, Winter Park

$1,550,000

Killarney Estates SubDv. ⋅ 32789 Zip Code

Rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term rental units — 8 studios and 4 one-bedroom/one-bath — plus a street-facing office suite fronting S. Orlando Ave. The thesis is straightforward: Winter Park generates year-round, non-theme-park demand — Rollins, Park Avenue, AdventHealth Winter Park, and the corporate and event traffic that fills the surrounding hotels at rates a 12-unit boutique operation can match without a hotel's cost structure.

271 S Orlando Avenue, Winter Park

$1,249,000

6 Beds ⋅ 6 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to your dream estate inside the highly sought-after, gated enclave of Lakeside Estates in Winter Park! This magnificent 2-story residence, built by Meritage Homes, spans an impressive 5,021 square feet of luxurious living space and features a commanding tile roof. Boasting a versatile layout of 6 bedrooms, 5 full bathrooms, and 1 half bath, this home showcases 2 separate primary suites one on each level providing an ideal setup for multi-generational living or an expansive guest retreat. Step through the entrance to be captivated by soaring high ceilings, fresh custom interior paint, premium engineered hardwood and tile flooring, and an open-concept flow flooded with natural light. The chef-inspired gourmet kitchen is an entertainer's masterpiece, equipped with brand-new quartz countertops, high-end stainless steel appliances, a generous island, and a seamless connection to the family room and sunny kitchen nook. Upstairs, a versatile bonus loft opens up endless possibilities for a media room or play space, supported by 2 dedicated indoor laundry rooms for ultimate convenience. Step outside to your private backyard paradise, complete with a covered lanai and a fully screened-in, sparkling custom pool and spa. Complete with an immaculate 3-car garage featuring a fresh protective floor coating, this property delivers executive comfort with easy access to top-rated schools, boutique shopping, fine dining, and all the historic charm of Winter Park. Schedule your private tour today!

1445 Via Sangro Place, Winter Park

$314,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code

WINTER PARK POOL HOME PRICE IMPROVEMENT Looking for a pool home you can truly make your own? Welcome to 1740 Puritan Ave in Winter Park! This property offers an exciting opportunity for the right buyer with the vision to unlock its full potential. Imagine relaxing by your private pool, entertaining family and friends, and creating your own backyard retreat! Whether you're searching for your next home or an investment opportunity, this property is full of possibilities. This home needs some TLC, but with the right care, creativity, and personal touches, it could become something truly special. Bring your imagination and make this pool home your own! Don't miss this opportunity to create the home you've been dreaming of in Winter Park. Schedule your private showing today!

1740 Puritan Avenue, Winter Park

$320,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 water heater, and updated plumbing. That means your weekends are for enjoying life where you call home. Fresh paint inside and out sets the tone the moment you pull up. Step inside to a bright, open floor plan where the kitchen, dining, and living spaces flow together for easy weeknight dinners and lazy Saturday mornings. The kitchen and bathrooms have been updated with a clean, modern feel, so all that’s left is to unpack. Out back, a fully fenced vinyl yard gives you privacy and room to play, garden, or host the cookout. A one-car garage adds plenty of storage. And the location? It’s hard to beat. You’re minutes from everything Winter Park has to offer, tucked right behind the new LifeTime fitness club, with exciting new development planned for the area. Homes this updated in this location don’t come around often. Schedule your showing today!

148 Oak Grove Rd, Winter Park

$750,000

5 Beds ⋅ 4 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code

Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition with; new interior paint, new carpet, 2 heating and cooling systems replaced in 2024! The open concept center island kitchen has upgraded counters, 42" cabinets and a double convection oven! Downstairs there is a formal living and dining room, an open concept kitchen, nice warm low maintenance ceramic tile, a convenient downstairs bedroom that would also be a great office/craft/game/guest room!! Upstairs are the other private bedrooms and a huge bonus theater/media/entertainment space.. The oversized primary bedroom is upstairs for complete privacy and has a well appointed bathroom as well as two walk in closets!! Come home and relax in your fenced back yard that has a peaceful forest behind it, set up a hammock and.... This fine gated community is located so close to so much, The University of Central Florida, Winter Park, Downtown Orlando, Trinity Preparatory Academy, The Masters Academy, The Geneva School, the Space Coast, Cocoa Beach and more!!

8061 Pleasant Pine Circle, Winter Park

$6,000,000

5 Beds ⋅ 7 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabinets, vanities, lighting, appliances, wallpaper to be CUSTOM SELECTED by Buyer. Also, layout of the rooms in in the photos may differ from the home to be built here.) The home is located on McKean Circle, one of the most sought-after, quiet, NO TRAFFIC streets in Winter Park… Very close walk to Park Avenue restaurants and shopping and Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home will include premium features, appliances, fixtures and finishes as follows: ELEVATOR, NATURAL GAS WHOLE HOUSE GENERATOR, WOLF/SUB ZERO appliances and wine cooler tower, built-in coffee maker, LUTRON RA3 SMART LIGHTING AND WIRING FOR BLINDS AND DRAPES, AUDIO/VIDEO, SMART HOME and SECURITY UPGRADES, WALLPAPER, special carpentry and architectural details, CEILING DETAILS with LED recessed/cove LIGHTING. FIRST FLOOR PRIMARY SUITE WITH WASHER/DRYER and two-person shower, additional GUEST SUITE FIRST FLOOR, OFFICE FIRST FLOOR, 12' FIRST FLOOR CEILINGS with 10’ DOORS. UPSTAIRS THERE EN SUITES plus large LOFT with wet bar and laundry room. Store-front window and door system with SMART GLASS (on demand opaque or clear), large 18’x10’ full-view garage door, circular driveway, heated swimmable pool with spa, plenty of pool deck space, and exquisite landscaping. A 6’ masonry-stucco wall with gates will encompasses the property. Outdoor living includes a large rear covered lanai with retractable screens and a large summer kitchen, pool-bath and outdoor shower. Enjoy two fireplaces: a linear fireplace (choose natural gas or electric) in living room and optional natural gas fireplace on the pool deck. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself. Call now to schedule your meeting with the Builder to get started on your new home today!

1011 Mckean Circle, Winter Park

$415,900

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bathroom home in Winter Park’s established Eastbrook community, with no HOA! New front entrance door and windows, recessed lighting in the spacious living room, and new stainless steel kitchen appliances bring fresh appeal to the home. Two sliding glass doors draw natural light into the living area and connect it to the covered, screened porch. A separate dining room sits alongside the kitchen, where ample cabinetry, bar seating, and a colorful subway tile backsplash create an inviting space for everyday meals and entertaining. Enjoy outdoor living with a covered, screened porch overlooking the fenced backyard, an above-ground pool for sunny Florida days, and room to relax, garden, or entertain. Two backyard storage sheds provide additional space for tools, outdoor equipment, and recreational gear. A standout feature is a separate room within the garage area, complete with a barn door, a dedicated A/C unit, and electrical outlets, an inviting space for a home office, hobby room, or creative projects. Major updates include a roof replaced (2023) and air conditioning (2021) and a water heater replaced (2021). Conveniently located near Advent Hospital, Full Sail University, Rollins College, downtown Winter Park, and shopping and dining, this home combines thoughtful updates with versatile spaces inside and out. Schedule your private showing today! Seller will not dismantle, or remove the pool. Buyer may retain the pool or arrange for its removal after closing at their own expense.

3409 Ferndell Drive, Winter Park

$230,000

3 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condominium SubDv. ⋅ 32792 Zip Code

Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of the sparkling community pools. Balcony features additional outside storage room. Dining/Breakfast Nook adjacent to Living Room & Kitchen. Kitchen features refrigerator, electric range, dishwasher, microwave, garbage disposal, pantry, and laundry closet with stackable washer/dryer. Nice sized bedrooms, see attached floor plan. Primary Suite features walk in closet, walk in shower and tile flooring. Guest Bath features tub & shower and tile flooring. Unit conveniently located at back of community by both community pools and tennis courts. Lovely shady, treed community with sidewalks, Clubhouse, two (2) Pools, BBQ areas, and Tennis Court. HOA Fees Cover: trash removal, water, internet only, amenities maintenance, landscaping, and roof. Community Docs and 2026 Budget available for review. Conveniently located to shopping, parks, restaurants, and major transportation routes. Property sold "AS IS", it won't last long!

216 Lewfield Cir Unit 216, Winter Park

$575,000

Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

$575,000

3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

$3,390,000

5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rarely found in such a desirable location. Positioned on an expansive homesite with an impressive architectural façade and meticulously curated landscaping, the home makes an unforgettable first impression before revealing an interior designed for both elevated entertaining and everyday living. A dramatic foyer with soaring 22-foot ceilings introduces an exceptional floor plan. To one side, a color-drenched private office is enveloped in custom trim work, while the formal dining room opposite features floor-to-ceiling windows and an elegant coffered ceiling. Beyond, the expansive living room is anchored by a stone-wrapped fireplace and framed by arched built-in shelving with integrated LED lighting. Natural wood beams add warmth and architectural character, creating a space that feels equally refined and inviting. The chef’s kitchen is a statement in both beauty and performance, showcasing custom cabinetry, quartz countertops, a professional Wolf gas range, and an oversized paneled Sub-Zero refrigerator. Overhead beams bring dimension to the space, while the adjoining breakfast nook, with custom built-in bench seating offers a charming setting for casual dining. A generously sized butler’s pantry and laundry room provide exceptional storage and functionality. Privately positioned on the main level, the primary suite opens directly to the covered lanai. Its spa-inspired bath is finished in beautiful marble and features dual vanities with floating mirrors, an expansive wet room with a freestanding soaking tub, and a fully customized wardrobe by award-winning Idelli Closets. Upstairs, a spacious loft creates an additional living area surrounded by four generously proportioned bedroom suites, each complete with a private bath and walk-in closet. A second laundry room adds convenience to the upper level. The outdoor setting rivals a private resort. A magazine-worthy summer kitchen anchors the expansive covered lanai, while retractable screens allow for comfortable year-round entertaining. Beyond, a heated pool and spillover spa are complemented by marble decking and additional green space. Just moments from Lake Sue, Park Avenue, Rollins College, East End Market, and zoned for highly sought-after Audubon Park School, this remarkable residence presents an exceptional opportunity to experience one of Winter Park’s most compelling homes.

1751 Glencoe Road, Winter Park

2219 Winter Woods Boulevard, Winter Park

$479,999

3 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

This 3-bedroom, 2.5-bath home offers approximately 1,776 square feet of living space on a spacious 0.24-acre lot. The two-story floor plan provides flexible living arrangements, while the generous yard offers outdoor space for relaxing, gardening, or entertaining. Additional features include central air conditioning and garage parking. Recent improvements include new roof, new HVAC, new water heater and much more.

2219 Winter Woods Boulevard, Winter Park

$985,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.

1611 Chestnut Avenue, Winter Park

$950,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

1411 Devon Road, Winter Park

$491,000

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 baths, and 2,308 sqft of modern, open-concept living. The main level flows from the foyer into a bright living/dining area and an island kitchen with granite-look counters, subway tile backsplash, and a full stainless appliance suite. Wood-look vinyl plank flooring throughout the living areas; carpeted bedrooms upstairs including a primary suite with tray ceiling, dual vanity, and glass-door walk-in shower with large-format tile. A versatile loft adds flexible living space. Step out to the covered lanai with ceiling fan overlooking a wooded view. 2-car garage plus a laundry room with sink and cabinetry. Enjoy resort-style community amenities — clubhouse, pool, playground, and park — minutes from Winter Park shopping and dining. HOA $333/mo. Call and schedule your showing today!

1407 Broad Wing Lane, Winter Park

$1,399,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an impressive two-story foyer and bright, open floor plan designed for comfortable living and effortless entertaining. A private fourth bedroom with a full bath is located near the entry, offering flexibility as a guest suite, home office, study, or secluded retreat. ***KITCHEN & MAIN LIVING AREAS: The gourmet kitchen serves as the heart of the home, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package with a 36-inch electric cooktop. Open to the spacious living and dining areas, it creates a seamless setting for everyday living and entertaining. ***PRIMARY SUITE & UPSTAIRS SPACES: The first-floor primary suite provides a peaceful retreat with a spa-inspired bath, dual vanities, a freestanding soaking tub, and a generous walk-in closet with custom shelving. A nearby laundry area adds convenience and efficiency. Upstairs, a spacious bonus room with a closet can function as a fifth bedroom, media room, game room, home office, creative studio. Two additional bedrooms feature walk-in closets and share a beautifully appointed bathroom with dual sinks. A second laundry room with a sink and abundant natural light adds further convenience. ***OUTDOOR LIVING: The covered lanai overlooks a sparkling pool and beautifully landscaped backyard, creating for the outdoor relaxation and entertaining. The entire covered porch features a motorized retractable screening system, allowing the space to be fully screened in. Low-maintenance artificial turf keeps the backyard looking lush and green year-round without the need for mowing, while an additional mosquito repellent system enhances outdoor enjoyment. ***LOCATION: Perfectly positioned near Winter Park's acclaimed shopping, fine dining, beautiful parks, and vibrant cultural attractions, this exceptional location also offers effortless access to I-4 and Downtown Orlando, Winter Park Village, Publix, Trader Joe's, and much more, making it easy to enjoy everything Central Florida Lifestyle. Make an appointment today before this beautiful, amazing home is gone!!!

1737 Indiana Avenue, Winter Park

$519,900

4 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Completely Renovated Winter Park Pool Home on a Spacious Corner Lot! Discover this beautifully renovated Winter Park home featuring a spacious corner lot, private swimming pool, and versatile living spaces. Located on a quiet dead-end street, this move-in-ready property combines updated interiors with inviting outdoor living. The interior features updated flooring, recessed lighting, and a bright living and dining area filled with natural light. The remodeled kitchen includes solid wood cabinetry with soft-close doors, elegant quartz countertops and backsplash, and stainless steel appliances. An additional family room provides flexible living space for relaxing, entertaining, or working from home. The home's flexible layout includes a separate-entry area that adds versatility. Outside, enjoy a private swimming pool, covered porch, and spacious yard. A side gate provides access for a boat, trailer, or work vehicle. Additional features include block construction, a two-car garage, a roof installed in 2019, and no HOA. Conveniently located near SR 436, Downtown Winter Park, Full Sail University, UCF, shopping, dining, and area schools. This property combines a renovated interior, private pool, spacious corner lot, and convenient access to local amenities in the Winter Park area.

731 Bongart Road, Winter Park

$2,100,000

Tuscania SubDv. ⋅ 32789 Zip Code

**A rare jewel in Winter Park's coveted Vias!** This oversized 0.36-acre lot (112' x 140') has been cleared and is ready for your custom estate home. Set on a charming brick street, it sits among multi-million dollar residences and lakefront estates, just steps from the Winter Park Racquet Club and close to Interlachen Country Club. Enjoy a quick drive to Park Avenue's boutiques and dining and the Winter Park 9 golf course. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. Opportunities to build in this sought-after neighborhood are few and far between, so bring your architect and your vision!

2036 Via Tuscany, Winter Park

4882 Tangerine Avenue Unit 4882, Winter Park

$185,000

2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Charming 2BD/1.5BA Wrenwood Condo in Winter Park! Adorable & affordable townhome-style condo with immaculate flooring, well maintained kitchen and appliances, brand-new water heater, and a recently replaced roof and AC unit ! You will also enjoy a lovely courtyard view. Enjoy 1,281 sq ft of comfortable living in a peaceful and highly sought-after location. Just steps away from the community pool and just a short drive to local shoppes and restaurants. Perfect starter home or investment opportunity- pets welcome! Call today to schedule your private showing!

4882 Tangerine Avenue Unit 4882, Winter Park

700 Melrose Avenue Unit M23, Winter Park

$354,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

$255,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park

$575,000

4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code

Virtually Staged. PRICED TO SELL, UNDER APPRAISED VALUE!! Come check out this GORGEOUS, SOLID 4/5 BR, 3 BA, 2,500+ sqft home in Winter Park with everything you need. This exceptional concrete block home was built to last, and major systems are current, updated, and documented. This home is MOVE-IN READY! Step inside and you’ll FEEL the difference. Fresh, neutral paint throughout and new vinyl flooring in both living areas create a light, welcoming backdrop. The kitchen, remodeled in 2023, shines with gleaming quartz counters, backsplash, shaker cabinets, and a breakfast bar. Upstairs, the HUGE master bedroom features a fireplace and balcony overlooking a large backyard—your personal private retreat! The bottom level offers GREAT flexibility—configure it as an IN-LAW SUITE with its own private bath and patio with French doors, or as a second living room and Florida room. Out back is where you’ll actually WANT to spend time with family and friends! Enjoy a naturally shaded deck every morning and evening. The oversized garage has a FAST EV charger. The property also comes with a large storage building with electricity AND a smaller shed. Major systems and structural upgrades include: HURRICANE-RATED double-pane windows and exterior doors opening to 4 feet! (2024), full home replumb (PEX-A), roof (5 years), electrical brought to current code (2025), water heater (2025), attic insulation with SOLAR FAN and sealed opening, and a high-efficiency Lennox AC (5-ton, 16 SEER) maintained yearly. Energy monitoring system included. Located in Seminole County’s top-rated school district, it is 15 minutes from Full Sail, 20 minutes from Rollins, and 30 minutes to UCF. This is the home that checks off all the boxes! MOTIVATED SELLER!!

2228 King Charles Court, Winter Park

$560,000

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code

No need to look further! This move-in-ready 4-bedroom, 2-bathroom home in Winter Woods is ready for you! Enjoy a fenced yard, no rear neighbors, lush greenery, and private country club views. Inside, you are greeted by a modern Scandinavian-inspired kitchen and split-bedroom floor plan. The primary suite offers a bonus room, walk-in closet, and private bath, while three additional bedrooms and a second full bath complete the home. All appliances are included, plus a generator that connects through the electrical panel—an ideal Florida feature during power outages. The owner is open to negotiating other select furnishings throughout the home. Conveniently located near Semoran Boulevard/SR 436, with easy access to Winter Park amenities. Schedule your showing of 2067 Poinciana Road today!

2067 Poinciana Road, Winter Park

330 W Morse Boulevard Unit 104, Winter Park

$1,379,000

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The interior space is professionally decorated with high end finishes and highly aesthetic. The turnkey floorplan offers open reception/waiting, full kitchen, bathroom, operating and pre-op rooms plus up to five private office spaces. Adjacent Unit 105 (separately listed in MLS) can also be purchased. Reserved parking spaces plus a wealth of street and public parking available nearby.

330 W Morse Boulevard Unit 104, Winter Park

328 W Morse Boulevard Unit 105, Winter Park

$1,420,000

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The turnkey space is professionally decorated with high end finishes and highly aesthetic.Floorplan offers five multi-purpose office, three patient rooms, open reception/waiting, lounge/kitchen area and common restrooms (secure lobby). The adjoining/adjacent unit 104 can be combined with this unit (see separate listing for Unit 104 in MLS) for a total of 3652 hsf. Reserved parking spaces plus a wealth of street and public parking available nearby.

328 W Morse Boulevard Unit 105, Winter Park

3307 Amber Wood Way Unit 106, Winter Park

$169,000

2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 06 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Whether you are looking for a home for yourself, or a great investment, don’t miss this opportunity close to Full Sail, UCF, and Valencia all while being zoned for Winter Park High! The property features 2 bedrooms with en-suite upstairs and a guest half bath downstairs. The unit comes nicely finished with laminate flooring throughout (no carpet!), granite countertops in the kitchen and a private gated back patio with storage! The community features a pool and the HOA covers all exterior maintenance along with the roof!

3307 Amber Wood Way Unit 106, Winter Park

$479,900

4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 14 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome home to 2020 Leanne Ct, a spacious pool residence offering versatile living and classic Florida charm in Winter Park! According to updated Seminole County tax and public records, this property features 4 bedrooms, 3 full bathrooms, and 2,088 square feet of functional interior living space set on an expansive 0.31-acre lot (13,504 sq ft). Inside, bright common areas feature formal living and dining spaces alongside a open central kitchen with breakfast bar overlooking a cozy family room. The desirable split-bedroom floor plan includes four well-proportioned bedrooms and three full baths, ideal for family accommodations, a primary suite, or dedicated home workspace options. Outside, enjoy a private backyard setting complete with a sparkling swimming pool and garden space—perfect for outdoor entertaining. Conveniently located near top-rated local schools, parks, shopping, and major routes

2020 Leanne Court, Winter Park

$649,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to 518 Gilbert Road, a beautifully updated 3-bedroom, 2-bath pool home offering 1,573 square feet of single-story living in the desirable Winter Park Pines neighborhood - with no HOA. Freshly installed front yard sod and mulch, mature palms, and distinctive stone accents create an inviting first impression. Inside, the home is light and bright with original terrazzo flooring and spacious living and dining areas. The living room features a wood-burning fireplace and architectural ceiling detail that adds character to the space. The beautifully updated kitchen offers white cabinetry, granite countertops, stainless steel appliances, a gas cooktop, convection oven, subway tile backsplash, modern lighting, and a large peninsula with bar seating. Both bathrooms have been renovated, including the primary bath with a walk-in shower and an updated guest/pool bath with convenient direct access to the backyard. Step outside to a private screened pool and an expansive pool deck, recently resurfaced in May 2026, providing plenty of room for outdoor dining, entertaining, and relaxing. Fully paid solar pool-heating panels extend the enjoyment of the pool, while the fully fenced PVC backyard adds privacy. A spacious two-car garage and outdoor storage provide additional room for everyday needs. Additional improvements include updated windows and sliding doors, replumbing, a newer HVAC system with gas/propane furnace, gas line, and partial updated ductwork. Enjoy an exceptional Winter Park location close to Cady Way Trail, Winter Park Pines Golf Club, Cady Way Park and its recreational amenities, Baldwin Park, and Downtown Winter Park. AdventHealth Winter Park, Rollins College, Full Sail University, UCF, shopping, dining, and everyday conveniences are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School, this move-in-ready pool home combines classic Winter Park character, thoughtful updates, and an outstanding location.

518 Gilbert Road, Winter Park

$1,699,900

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Under Construction. Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringing warm contemporary design and effortless living to Winter Park. Offering 2,661 square feet, four bedrooms, three-and-a-half baths and a two-car garage, the home pairs a refined architectural presence with light-filled interiors and a highly considered floor plan. At the heart of the home, an expansive open-concept living space brings together the kitchen, dining and family areas for an easy sense of connection. The designer kitchen makes a statement with an oversized island, extensive cabinetry, integrated appliances and sophisticated finishes, while large windows and glass doors invite natural light throughout the main living areas. A first-floor guest suite offers added flexibility for visitors, a private office or multigenerational living. Upstairs, the primary suite is joined by two additional bedrooms, creating a comfortable separation between everyday living and private spaces. The primary retreat features a generous walk-in closet and a spa-inspired bath designed with a soaking tub, dual vanities and an oversized shower. Outside, the covered lanai extends the living space into the backyard, overlooking a private pool and landscaped surroundings, an inviting setting for relaxed afternoons, entertaining and year-round Florida living. With its soft neutral palette, natural textures, modern detailing and thoughtfully connected spaces, 2613 Lafayette Avenue offers a fresh take on new construction in Winter Park, sophisticated without feeling overly formal and designed for the way people live today. Ideally situated near the area’s dining, shopping, parks and everyday conveniences, the residence pairs the ease of new construction with the lifestyle and sense of place that make Winter Park so desirable.

2613 Lafayette Avenue, Winter Park

$575,000

3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Welcome to 112 Bell Place, a spacious 3-bedroom, 2-bath home offering 2,253 square feet in an established Winter Park neighborhood. Tucked away on a quiet cul-de-sac with a large lot and minimal through traffic, this home offers a great opportunity for buyers looking to move right in and make updates over time, or for an investor looking for a property with great bones and plenty of potential. Inside, you’ll find generous living spaces including a living room with laminate wood flooring and vaulted ceiling, plus a large family room featuring a brick accent wall. The kitchen offers solid wood cabinetry, cooktop, oven and microwave with plenty of opportunity to update and make it your own. All three bedrooms feature built-in closets, while the primary suite includes wood-look laminate flooring and a private bath with shower. The guest bath offers a tub and tile flooring. Additional features include a one-car garage, exterior laundry area, and a hall closet already plumbed for a washer and dryer should the new owner prefer to bring the laundry indoors. With its spacious floor plan, large lot and solid foundation for future improvements, this home has so much potential. Conveniently located in Winter Park and currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School, this is a great opportunity to get into a sought-after area and add your own style over time. Move in now, renovate at your own pace, and make this Winter Park home your own! Buyer to independently verify school zoning.

112 Bell Place, Winter Park

$650,000

4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code

Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park

3032 Antique Oaks Circle Unit 145, Winter Park

$134,999

1 Beds ⋅ 1 Baths ⋅ Parkview Village Condominium SubDv. ⋅ 32792 Zip Code

Investment opportunity in the heart of Winter Park! This tenant-occupied 1-bedroom, 1-bath condo in Parkview Village offers 749 square feet of comfortable living space with an open living and dining area, functional kitchen, in-unit washer and dryer, and sliding glass doors leading to a private screened patio. The community features a pool and clubhouse, while the convenient location provides easy access to Full Sail University, UCF, SR-436, SR-417, shopping, dining, and everyday conveniences. With a tenant already in place, this property offers an excellent opportunity for an investor looking to add an income-producing Winter Park condo to their portfolio.

3032 Antique Oaks Circle Unit 145, Winter Park

$325,000

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview Heights community, this 3-bedroom, 2-bath concrete-block home offers 1,344 square feet of living space with a functional single-story floor plan and plenty of potential for a buyer looking to make a home their own. Inside, the home features tile flooring throughout the main living and dining areas, vaulted ceilings, ceiling fans, and a split-bedroom layout that provides added separation and flexibility. The kitchen is equipped with a convection oven, dishwasher, microwave, and refrigerator, while indoor washer and dryer hookups add everyday convenience. Step outside through the covered rear entry to a brick-paver patio overlooking the fully fenced backyard. Mature trees provide natural shade, while the outdoor space offers plenty of room for entertaining, gardening, pets, or simply enjoying the Florida lifestyle. A one-car carport provides covered parking, and the property is connected to public water and sewer. One of the property's biggest advantages is its Winter Park location. Enjoy convenient access to shopping, restaurants, parks, major roadways, downtown Winter Park, Park Avenue, College Park, and surrounding Orlando destinations while still coming home to an established residential neighborhood. With NO HOA, solid concrete-block construction, a fenced yard, and a sought-after 32789 address, 310 Granada Drive presents an exciting opportunity for an owner-occupant, investor, or buyer looking to renovate and add their personal style. Schedule your private showing and discover the possibilities this Winter Park property has to offer!

310 Granada Drive, Winter Park

302 Lewfield Circle Unit 302, Winter Park

$140,000

1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

ENJOY THE WINTER PARK LIFESTYLE from this charming one-bedroom, one-bath condo offering low maintenance living in a convenient Central Florida location. Step inside to a bright and comfortable floor plan with a private second floor balcony that extends the living space outdoors, perfect for sipping coffee, reading a book, or enjoying the Florida weather. The community offers a refreshing pool and clubhouse, providing additional spaces to relax and enjoy. Located just minutes from the shops and restaurants of Park Avenue, Rollins College, local parks, and everyday conveniences, you’ll have easy access to everything that makes Winter Park such a desirable place to call home. A great opportunity for a full-time residence, seasonal getaway, or anyone looking to enjoy a simplified lifestyle in Winter Park! Listing photos have been virtually staged for visualization and illustrative purposes only. The property is currently vacant and move-in ready.

302 Lewfield Circle Unit 302, Winter Park

$900,000

4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to Waters Edge at Hawks Crest, one of Winter Park’s premier gated communities! This beautifully appointed 4-bedroom, 3-bath home offers nearly 3,000 square feet of thoughtfully designed living space, exceptional curb appeal, and an outdoor entertaining area that truly sets it apart. Step inside to a welcoming foyer flanked by a formal dining area and a versatile formal living room with double doors—perfect for a home office, den, or flex space. At the heart of the home is an impressive gourmet kitchen featuring quartz countertops, a large center island with stainless undermount sink, wall oven/microwave combination, cooktop with stainless steel range hood, metallic hexagon tile backsplash, modern pendant lighting, and a technology-equipped refrigerator. The kitchen flows seamlessly into the casual dining and family room, creating an open-concept gathering space filled with natural light from oversized triple sliding glass doors. An electric shade provides added privacy and makes movie nights a breeze. The spacious primary suite offers a striking stacked-stone entry and a separate flex area ideal for a sitting room, office, nursery, or workout space, with direct access to the lanai. The ensuite bath features dual quartz vanities, a soaking tub, large tiled shower, private water closet, and an impressive custom-designed walk-in closet with abundant storage. The split-bedroom floor plan provides three additional bedrooms, two full baths—including a convenient pool bath—and a dedicated laundry room. The garage offers additional storage racks, while solar-powered Tesla panels and two Powerwalls add another notable feature to the home. The showstopper is the expansive screened lanai, designed for year-round Florida living and entertaining. Multiple conversation and dining areas, an outdoor kitchen, TV area, oversized premium spa with additional jets, and app-controlled lighting create the perfect setting for everything from intimate evenings to large gatherings. A 6-foot privacy fence completes this private backyard retreat. Residents of Hawks Crest enjoy an impressive collection of community amenities, including a clubhouse with indoor and outdoor entertaining spaces and grills, resort-style pool, splash pad, playgrounds, fitness center, putting green, outdoor games, dog park, neighborhood parks, and access to a community dock on Lake Howell.

2052 Wood Thrush Lane, Winter Park

$2,125,000

5 Beds ⋅ 5 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. The Hawthorn, an exceptional new custom residence by FG Schaub Custom Homes, located at 918 Enclave Place within The Enclave, a premier boutique community in the heart of Winter Park. Offering 5 bedrooms, 4.5 bathrooms, and 3,713 square feet of thoughtfully designed living space, this two-story home blends timeless architectural appeal, refined finishes, and a highly functional layout designed for modern living. The thoughtfully designed floor plan offers the convenience of a spacious first floor primary suite with a well-appointed bath and generous walk-in wardrobe, along with an additional first-floor guest suite with an en-suite bath. The open-concept kitchen, dining, and gathering areas create a natural flow for everyday living and entertaining, while the second floor provides three additional bedrooms, two full bathrooms, and a versatile gathering loft ideal for a media room, playroom, or additional living space. Designed to embrace Florida's indoor-outdoor lifestyle, the home features a covered lanai overlooking a private swimming pool and fully fenced backyard. The summer kitchen, complete with grill and refrigerator, creates an inviting setting for outdoor dining and entertaining. Throughout the home, elevated specifications and thoughtful details include high-performance, low-E double-pane windows, 8-foot solid-core interior doors, a tankless gas water heater, premium Wolf and Sub-Zero appliances, and designer-selected finishes with a curated palette of colors and materials. Every detail reflects the craftsmanship and quality synonymous with FG Schaub Custom Homes. The Enclave is an intimate collection of just 23 thoughtfully designed residences nestled beneath mature oak canopies. Ideally situated near Phelps Park, the YMCA, and multiple dining and shopping options, residents enjoy a charming residential setting with convenient access to downtown Winter Park's celebrated restaurants, boutiques, and cultural attractions. As a new home to be built, buyers have the opportunity to personalize select design finishes and explore certain floor plan modifications. Additional upgrade opportunities may include a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Experience the opportunity to create your dream home in one of Winter Park's most desirable locations, where architectural character, exceptional craftsmanship, and a connected lifestyle come together.

918 Enclave Place, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park

$850,000

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

$169,900

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-bath condo offers 645 SF of move-in-ready living in desirable Lakeside Manor on beautiful Lake Killarney. Enjoy easy first-floor access, peaceful park-like grounds, a sparkling lakefront pool, clubhouse, community boat access and docks—all just steps from your door. The location is exceptional—minutes from Winter Park Village, Park Avenue, Rollins College, shopping, dining and entertainment, with quick access to I-4 and Downtown Orlando. Perfect as a primary residence, second home or low-maintenance getaway. UPDATED. GROUND FLOOR. LAKEFRONT COMMUNITY. PRIME WINTER PARK LOCATION. Come see why Lakeside Manor remains one of Winter Park’s best-kept secrets!

2500 Lee Road Unit 123, Winter Park

$290,000

2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code

Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park

$419,900

3 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern improvements, featuring beautiful hardwood floors, crown molding, a fireplace, and plenty of natural light throughout. The bright enclosed Florida room provides flexible space for a home office, sitting area, playroom, or additional entertaining space. The updated kitchen offers dark cabinetry, stone countertops, stainless steel appliances, and contemporary finishes. Major improvements include a brand-new roof installed in 2026, along with updated electrical, plumbing, and HVAC systems completed in 2025. These recent improvements provide added value and peace of mind for the next owner. The interior laundry room adds everyday convenience, while the covered rear porch creates a comfortable place to relax and enjoy the outdoors. The fenced backyard offers room for entertaining, gardening, pets, or creating a private outdoor retreat. Enjoy a prime location near A-rated schools, Dubsdread Golf Course, College Park, downtown Winter Park, AdventHealth, shopping, dining, and major roadways. With no HOA and easy access to some of Central Florida’s most popular neighborhoods, this home delivers the character, location, and major updates that make it stand out.

712 Baffie Avenue, Winter Park

200 Saint Andrews Boulevard Unit 704, Winter Park

$159,000

1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code

LOCATION, LIFESTYLE & OPPORTUNITY IN THE HEART OF WINTER PARK! Welcome to 200 Saint Andrews Boulevard #704, a charming top-floor, 1-bedroom, 1-bath condominium in the established Four Seasons Condominiums of Winter Park. Whether you’re searching for a primary residence, low-maintenance Winter Park retreat, or investment property, this condo offers an incredible opportunity just minutes from Rollins College, Park Avenue, and Downtown Winter Park. Located on the second and top floor, the residence offers a comfortable and functional layout with beautiful wood flooring throughout the living room and bedroom. The spacious living area flows into the dining space and kitchen, while the primary bedroom features a generous walk-in closet. Two separate entrances add convenience, and the oversized screened-in balcony provides the perfect place to enjoy morning coffee, unwind at the end of the day, or enjoy Florida’s year-round outdoor lifestyle. A private storage closet on the balcony provides additional space, and abundant community parking makes everyday living easy. Four Seasons is an established approximately 20-acre condominium community located within the City of Winter Park. Residents enjoy three community swimming pools, tennis courts, shuffleboard, a clubhouse with library, community laundry facilities, and more. COA INCLUDES WATER, TRASH, SEWER, PEST CONTROL, EXTERIOR AND GROUNDS MAINTENANCE. For buyers who value LOCATION, this one is hard to beat. Rollins College, iconic Park Avenue, and Downtown Winter Park are just minutes away, providing easy access to some of Central Florida’s best restaurants, boutiques, coffee shops, museums, community events, and entertainment. Enjoy nearby outdoor recreation at Cady Way Trail, Ward Park, Showalter Field, and the YMCA, plus convenient access to AdventHealth Winter Park, Baldwin Park, Winter Park Village, Downtown Orlando, I-4, and major Central Florida roadways. For investors, the combination of a Winter Park address, proximity to Rollins College and major employment, healthcare, shopping, dining, and recreation destinations makes this property an option worth considering for a long-term real estate investment. For an owner-occupant, it offers the opportunity to enjoy the Winter Park lifestyle in a low-maintenance condominium setting. Enjoy the convenience of being close to everything while coming home to an established community in one of Central Florida’s most recognized locations. Schedule your private showing and discover the possibilities at Four Seasons Winter Park!

200 Saint Andrews Boulevard Unit 704, Winter Park

$3,250,000

5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park

$850,000

Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Bring your vision to life in Winter Park. Situated on N Phelps Avenue, this approximately .24-acre property offers a rare opportunity to build new in an area surrounded by custom homes, luxury residences, and ongoing redevelopment. Offered for its land value, this property is well suited for builders, investors, developers, or anyone ready to create a home designed around their own style and needs. The 75-foot frontage with 140-foot depth provides flexibility for a variety of architectural designs and potential for outdoor living, a pool, and backyard space. With new construction continuing to reshape the surrounding area, 870 N Phelps presents an exciting opportunity to secure a sizable homesite and build from the ground up.

870 N Phelps Avenue, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Virtually Staged. Pre-Construction. To be built. POOL + SAUNA • DOUBLE PRIMARY SUITES • 3-CAR GARAGE • CUSTOM NEW CONSTRUCTION IN WINTER PARK Pool, sauna, double primary suites and a 3-car garage set the tone for this custom pre-construction residence planned for 2007 Edwin Blvd in Winter Park. Designed for elevated indoor-outdoor living, this 4-bedroom, 3.5-bath home brings together a flexible floor plan, distinctive amenities and carefully selected finishes in a new custom build. The double primary-suite configuration creates two dedicated primary retreats, adding versatility to the home’s layout. Interior specifications include 10-foot ceilings, Level 5 drywall finish, porcelain tile flooring, 5-inch baseboards, granite countertops and wood cabinetry. A dedicated butler pantry extends the kitchen with additional preparation, serving and storage space. Outdoor living is an integral part of the design, with a private pool and sauna incorporated into the planned residence. The 3-car garage provides generous vehicle and storage capacity, while the exterior architecture combines stucco and Hardie siding. The residence is planned with approximately 3,314 square feet under A/C and 4,111 total gross square feet, providing substantial interior and covered space while maintaining the functionality of the 4-bedroom layout. Located in Winter Park, the property offers convenient access to the Aloma Avenue corridor and surrounding restaurants, coffee shops, grocery stores, retail, parks and everyday services. Downtown Winter Park, Park Avenue, Central Park and Rollins College are also within the greater Winter Park area. For buyers searching for a new construction home in Winter Park with a pool, sauna, double primary suites, 3-car garage, butler pantry and custom finishes, 2007 Edwin Blvd brings these sought-after features together in one thoughtfully planned residence. Architectural plans, site plan and exterior elevations illustrate the proposed home, pool and garage configuration. Property is offered pre-construction. Final square footage, dimensions, materials, finishes and specifications are subject to final plans, builder selections and modifications. Schedule a private consultation to review the plans, proposed finishes and design details and explore the opportunity to make this custom Winter Park residence your next home.

2007 Edwin Boulevard, Winter Park

$1,950,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code

Under Construction. Set in Winter Park’s desirable Kenilworth Shores, this exceptional new residence blends timeless architecture, elevated finishes and thoughtfully designed interiors tailored to the modern Florida lifestyle, with anticipated completion by end of the year. Offering five bedrooms and four and a half baths, this property features a highly versatile floor plan with a first-floor primary suite and beautifully connected indoor and outdoor living. The main level is centered around an expansive open-concept kitchen and living area, complemented by a dedicated dining room that provides an elegant setting for more formal gatherings. The chef’s kitchen is appointed with a premium Thermador appliance package, generous central island and walk-in pantry, creating a highly functional setting for everyday living and entertaining. A nearby mudroom adds valuable storage and convenience. The spacious living room opens directly to the covered lanai, creating a seamless transition between interior and exterior. The first-floor primary suite offers a private retreat with a spacious bedroom, luxurious en-suite bath and expansive walk-in closet. A second bedroom and full bath are also on the main level, providing flexibility for guests, a private office or additional living space. Upstairs, three additional bedrooms are complemented by two full baths and a generous loft. The versatile loft can be tailored to a variety of needs, whether used as a media room, playroom, second lounge or workspace. A dedicated laundry room completes the upper level. Designed to embrace the Florida lifestyle, the covered lanai overlooks a private saltwater pool and spa, while the summer kitchen creates an inviting setting for outdoor dining and entertaining. The seamless connection between the main living areas and outdoor spaces makes the home equally suited to relaxed everyday living and effortless entertaining. Ideally in Winter Park, this residence is within the sought-after Brookshire Elementary, Glenridge Middle and Winter Park High School zones. Park Avenue’s renowned restaurants, boutique shopping, galleries and charming streetscape, along with AdventHealth Winter Park, are conveniently nearby. Cady Way Park is also nearby, offering a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and biking trails. With its combination of new construction, timeless design, premium appliances, flexible living spaces and exceptional indoor-outdoor flow, 513 Dunraven Drive presents a distinctive opportunity to experience Winter Park living. Private showings are being scheduled now.

513 Dunraven Drive, Winter Park

$724,900

4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park

$2,500,000

5 Beds ⋅ 5 Baths ⋅ Jenkins Second Add SubDv. ⋅ 32789 Zip Code

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-and-a-half bathrooms, this custom residence seamlessly blends striking contemporary lines with exceptional everyday functionality. The heart of the home is a culinary dream chef's kitchen, anchored by an oversized center island and premium quartz countertops. It comes fully equipped with custom 42-inch wood cabinetry, a dedicated walk-in pantry, and high-end appliances, including a 48-inch refrigerator, a 36-inch induction cooktop with a vented hood, a built-in microwave, a dishwasher, and double convection ovens. Entertain effortlessly in the adjacent formal dining room or mix drinks at the wet bar, which features a built-in wine chiller to keep your collection perfectly preserved. Designed for ultimate privacy, the first-floor primary suite serves as a peaceful sanctuary, complete with a spa-inspired bathroom featuring a spacious walk-in shower, a standalone soaking tub, and a thoughtfully organized his-and-hers walk-in closet with abundant storage. A generous guest retreat with a private full bath is also conveniently located on the main level. Ascend to the second floor to find soaring 11-foot ceilings and three additional well-appointed bedrooms, each designed with privacy and direct full-bath access in mind. Step through oversized sliding glass doors to transition into your private outdoor oasis, effortlessly expanding your living space into the open air. This smart-home-ready masterpiece comes equipped for integrated lighting, audio, and security, alongside pre-installed exterior accent lighting, security cameras, and a full-property irrigation system. Perfectly positioned for an elevated Florida lifestyle, this home is less than five minutes from the premier Interlachen Country Club, walking distance to Phelps Park, and just ten minutes from the world-class boutique shopping and fine dining along Park Avenue.

1760 Oakhurst Avenue, Winter Park

$355,000

3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code

Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly maintained. With an open and spacious floor plan is great for family activities and entertaining. NEW HV/AC AND NEW WATER HEATER. kitchen features all stainless steel appliances, large island great for prep with seating for "4" or more on the oposite side. The large slider leads out to your 5' X 11" private lani, allows natural light to fill the entire space. There is a first floor powder room for convenience for you and your guest. Second floor laundry closet for your convenience. Your oversize primary bedroom features a spacious walk-in closet and ensuite with large vanity and double sinks. There are "2" additional guest bedrooms. The home has a one car garage with an extended pad for a second car. the NEW water heater is located in the garage. The A/C is also NEW. Aloma Trails is convenient to shopping directly accross the street from the complex. minutes from Aloma (426), 417, UCF, Full Sail, Rollins, a Park Ave., Airport and Beaches. SELLER IS MOTIVATED

7498 Aloma Pines Court, Winter Park

$398,000

3 Beds ⋅ 2 Baths ⋅ Bridgewater SubDv. ⋅ 32792 Zip Code

PHENOMENAL DEAL, newer updates INCLUDE: beautifully renovated 4-bedroom, 2-bathroom, two car garage home that perfectly blends modern design with everyday comfort. From the moment you step inside, you’ll appreciate the open-concept floor plan, thoughtfully designed to create a bright, spacious atmosphere that’s perfect for both entertaining and daily living. This move-in-ready home features custom finishes throughout, including stylish fixtures, updated flooring, and a beautifully remodeled kitchen and living space. The expansive primary suite offers a private retreat with a generous bedroom and a stunning ensuite bathroom designed with comfort and luxury in mind. Additional updates include newer roof, AC, water heater, Updated kitchen and bathrooms, The Kitchen is Large with all major appliances: Fridge, Stove, and Dishwasher. You don't want to miss this opportunity to make this house your home!

7786 Fox Knoll Place, Winter Park

$140,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Welcome to this bright and beautifully updated second-floor condo located in one of Winter Park's most desirable communities! This 2-bedroom, 1-bathroom residence offers the perfect blend of comfort, modern upgrades, and an unbeatable location. Updated Kitchen: Features dark wood cabinetry, light quartz counter tops, black and stainless-steel appliances, a modern commercial-style faucet, and an in-unit washer/dryer set. Spacious Living & Bedroom Areas: Enjoy durable luxury vinyl plank flooring throughout the main areas, bright natural light, and modern finishes. Renovated Bathroom: Outfitted with a updated vanity, chic black hardware, and stylish lighting fixtures. Private Balcony: Relax outdoors on your private covered balcony with peaceful views of the lush green courtyard and community grounds. Resort-style sparkling swimming pool with expansive sun deck. Well-maintained grounds with mature landscaping and tropical palm trees. Quiet, well-kept building entrance and grounds. Situated right off Lee Road, you are just minutes away from top dining, shopping, and entertainment spots. Enjoy close proximity to Park Avenue in Downtown Winter Park, Rollins College, I-4 access for an easy commute to Downtown Orlando or major attractions. Local parks, lakes, and grocery stores. Whether you are looking for a primary residence or a strong investment opportunity in the booming Central Florida market, this move-in-ready condo is a must-see! Schedule your private tour today!

1695 Lee Road Unit C206, Winter Park

$759,900

3 Beds ⋅ 3 Baths ⋅ Golfside Sec 02 SubDv. ⋅ 32792 Zip Code

Welcome to 1003 Golfside, a fully reimagined single-story pool home in the Winter Park area, set beneath a mature oak canopy on a beautifully landscaped lot. Major updates include a NEW ROOF (2025) and a RENOVATED POOL (2025). Inside, the open-concept layout features high-gloss marble-look porcelain tile, recessed lighting, designer ceiling fans and built-in ceiling speakers. The chef's kitchen offers high-gloss cabinetry, quartz countertops with a full-height quartz backsplash, built-in wall oven and microwave, induction cooktop and a large quartz island with bar seating. The living area showcases a custom accent wall, a brick fireplace and French doors to the pool. Bathrooms are updated with quartz vanities, vessel sinks, frameless glass showers and marble-look tile. The spacious primary bedroom offers plantation shutters and room for a sitting or office area. Outside, enjoy a private fenced backyard with the renovated pool, composite decking and an L-shaped outdoor kitchen with sink and grill. Just minutes from Baldwin Park, where you can enjoy the 2.5-mile Lake Baldwin Trail, Lake Baldwin Park with its dog beach, playground and boat ramp, the Cady Way Trail, and the Village Center's restaurants, shops and community events. Schedule your private showing today!

1003 Golfside Drive, Winter Park

173 Scottsdale Square Unit 173, Winter Park

$100,000

1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code

INVESTMENT OPPORTUNITY! Add this well-maintained condo to your investment portfolio or make it your next income-producing property. Featuring a functional layout, neutral finishes, easy-care flooring, stainless-steel appliances, and plenty of natural light, this unit offers an attractive and low-maintenance option for investors. The comfortable living area flows to the outdoor space through sliding glass doors, creating a bright and inviting atmosphere. Conveniently located near shopping, dining, major roadways, and everyday necessities. Whether you're expanding your rental portfolio or looking for your next investment opportunity, this condo is worth a look. Schedule your showing today!

173 Scottsdale Square Unit 173, Winter Park

$200,000

32792 Zip Code

This well established Massage Therapy School has been serving Central Florida for over 30 years, of offering a strong reputation and a fully operational educational environment. With consistent enrollment and a trusted name in the community, it presents a rare opportunity for a buyer seeking a turnkey business in the wellness and education sector. The school currently operates three active classes, both day and evening, with the capacity to add a fourth class to increase revenue. The facility is fully equipped and thoughtfully designed, featuring two conference style classrooms, multiple massage therapy rooms that can be rented for additional income, two bathrooms, a fully equipped administrative office, a cafeteria for students and instructors, dedicated storage rooms, and a library store offering class books and massage therapy products for sale. Its location in a high visibility plaza provides excellent exposure and accessibility. This is an ideal opportunity for an investor or licensed massage therapist looking to expand, rebrand, or scale through modern advertising and marketing strategies. With its solid foundation, long-standing reputation, income producing layout, and retail component, the school is ready for a new owner to elevate it and unlock its full growth potential.

450 N Lakemont Ave, Winter Park

1250 S Denning Drive Unit 119, Winter Park

$265,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations. Recent updates include new luxury vinyl flooring throughout the kitchen and great room, new carpeting in both bedrooms, fresh interior paint, and a recently redone screened-in porch with a refreshed frame and new screening. The thoughtfully updated kitchen features shaker-style cabinetry, granite countertops with breakfast bar, and stainless steel appliances. Additional features include remodeled bathrooms, low-Emissivity windows and sliding glass door, crown molding, updated baseboards and light fixtures, Nest thermostat, A/C replaced in 2018, and water heater replaced in 2019. Enjoy Florida living from the screened-in porch with convenient direct access to the community pool, onsite laundry facility, and mailroom. The first-floor corner location offers added privacy, comfortable single-level living, and a designated parking space.

1250 S Denning Drive Unit 119, Winter Park

$479,900

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

$429,900

3 Beds ⋅ 2 Baths ⋅ Winter Park Estates Sec 5 SubDv. ⋅ 32792 Zip Code

Welcome home to this charming Winter Park residence located in the desirable 32792 zip code. Nestled on a quiet street at 2818 Ambergate Road, this inviting property offers the perfect blend of comfort, style, and everyday convenience. Step inside to discover a bright, open floor plan featuring original Terrazzo, generous living spaces, natural light, and a warm atmosphere ideal for both relaxing and entertaining. Newer roof 2023. The private backyard provides a wonderful outdoor oasis for weekend gatherings or peaceful morning coffee. Situated just minutes from top-rated schools, local parks, bustling shopping centers, and vibrant downtown Winter Park, this move-in-ready home puts the best of Central Florida right at your doorstep. Don't miss this exceptional opportunity - Schedule your private showing today!

2818 Ambergate Road, Winter Park

$319,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Pointe 02 Ph 01 SubDv. ⋅ 32792 Zip Code

This ONE STORY Villa-Style condo is in a nice, quiet, Winter Park community close to everything! The open layout has a formal dining room and living room with a brick fireplace! The vaulted ceilings give it a large airy feeling especially with two atriums full of natural light! Sliding glass doors lead to a rear screened in porch from the Living Room. A perfect place to enjoy your morning coffee! The primary suite has large glass doors, going out to the private open air patio and garden area! The Kitchen atrium allows even more sun light and a place for your favorite plants! The kitchen cabinets and the movable coffee bar give plenty of storage space! Or you may want a two seater table and chair instead!! The beautiful granite speaks for itself. The best part is yet to come!! This condo has a 2 car Garage with a wall of storage cabinets. Plenty of room for your vehicle w added storage! Tile Roof new (2025). Membrane Roof new (2020). Re-piped (2013). AC new inside/out (2018). Electrical checked at move in (2013). You are minutes from Ward Park, Cady Way Trail and Pool, Crosby Wellness Center and Advent Health Winter Park Hospital, plus numerous stores and restaurants! This is a VERY QUIET 55+ community which allows no leasing through their BYLAWS !

192 Balfour Drive Unit 2, Winter Park

$2,089,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home pairs classic double-gallery porches with 3,479 sq ft of open, light-filled living in Winter Park's established Charmont neighborhood. Inside, rich hardwood floors, tray ceilings, crown molding and walls of French doors set the tone. The formal living and dining rooms open to a spacious great room and a chef's kitchen with an oversized granite island seating six, statement pendant lighting, stainless steel appliances, double wall ovens, abundant cabinetry, a walk-in pantry and a separate coffee/beverage bar with wine fridge. The main-level primary suite is a true retreat with a tray ceiling, French doors to the covered lanai, a custom walk-in closet and a spa bath with a freestanding soaking tub, dual vanities and a frameless glass shower. Upstairs, a large loft offers flexible space for a media room, gym or home office, with French doors to the second-story porch, along with generously sized secondary bedrooms. Step outside to your private backyard oasis: a covered lanai with outdoor kitchen, bar seating and ceiling fans overlooks the paver pool deck, sparkling pool with raised spa and fire bowls, all framed by mature landscaping and privacy fencing. Additional highlights include a laundry room with sink and cabinetry, a two-car garage and a paver driveway. Just half a mile from Audubon Park K-8, with Lake Baldwin Park, Mead Botanical Garden, East End Market, Baldwin Park Village and downtown Winter Park's shops and restaurants all close by, and about 4 miles to downtown Orlando.

1951 Winter Park Road, Winter Park

100 S Virginia Avenue Unit 201, Winter Park

$1,450,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

$2,990,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-square-foot homesite in the fast growing Kenilworth Shores neighborhood. Striking curb appeal introduces the home, while a marble mosaic foyer provides an elegant first impression and leads into the expansive great room. At the center of the living space is a dramatic custom entertainment wall featuring illuminated built-in shelving and a sleek electric fireplace. The adjoining dining room is equally impressive, complete with an oversized dry bar, wine refrigerator, and glass-front cabinetry, creating the perfect setting for hosting family and friends. The designer kitchen makes a statement with Taj Mahal countertops, a marble mosaic backsplash, custom cabinetry, and a full suite of Thermador appliances, including a paneled built-in refrigerator. A massive butler’s pantry extends the kitchen’s functionality with abundant storage and preparation space, a second microwave and oven, and an additional dishwasher, making entertaining effortless. The downstairs primary suite offers a private retreat accented by warm wood beams and separate his-and-hers closets. Its jaw-dropping spa-inspired bathroom is wrapped in 12-by-24-inch marble tile and features dual vanities, a freestanding soaking tub, and an oversized walk-in shower with LED-illuminated niches. A dedicated home office is also located on the main level, providing a quiet and refined space for working from home. Upstairs, a massive bonus room creates a flexible second living area ideal for movie nights, a game room, or a children’s retreat. Four additional spacious bedrooms offer comfort and privacy for family and guests, while an upper-level balcony provides another inviting place to unwind. The outdoor living spaces are designed to take full advantage of the oversized lot. A large covered lanai with a complete summer kitchen overlooks the resort-style pool and spa, all framed by an elegant marble deck. Beyond the pool, the expansive backyard offers valuable green space for recreation, entertaining, or relaxation. Additional highlights include a complete impact-rated window and door package for added efficiency and peace of mind. Perfectly positioned near Cady Way Park, AdventHealth Winter Park, and just a golf-cart ride from Park Avenue, this extraordinary new residence presents a rare opportunity to experience uncompromising luxury, exceptional space, and the very best of the Winter Park lifestyle.

532 Langholm Drive, Winter Park

$1,890,000

4 Beds ⋅ 4 Baths ⋅ Parklando 03 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more than 3,300 square feet of fully remodeled living space in Winter Park’s 32789 zip code, zoned for the highly sought-after Audubon Park School K–8 and Winter Park High School; all at a price below appraised value. Welcome to 2614 Parkland Drive, a completely reimagined luxury residence where sophisticated interiors meet resort-style Florida living. Extensively remodeled in late 2022 and topped with a brand-new architectural barrel tile roof, this home combines timeless character with modern finishes and major system upgrades. Inside, solid light-oak flooring, custom railings, and an open-concept layout create a warm, elevated feel throughout. The chef’s kitchen anchors the main living space with quartz countertops, full-height designer tile, abundant cabinetry, and a layout designed equally well for entertaining and everyday living. Step outside and the home transforms into a private resort. The custom heated pool and spa are finished in striking Caribbean-blue tile and surrounded by dramatic waterfalls, dual natural-gas fire features, porcelain privacy walls, and a built-in grill—creating an exceptional setting for entertaining or unwinding at home. The first-floor primary suite opens directly to the outdoor oasis. Upstairs, three oversized bedrooms are joined by a spacious loft and private patio; offering flexible space for family, guests, an office, or additional entertaining. Additional features include a brand-new barrel tile roof, dual tankless water heaters, central vacuum, natural-gas appliances, and extensive updates throughout. With more than 3,300 SF, a luxury pool and spa, extensive renovations, highly desirable school zoning, and a 32789 address, this home represents an exceptional opportunity in the Winter Park market. Luxury. Location. Lifestyle. And priced below appraised value.

2614 Parkland Drive, Winter Park

1602 Alabama Drive Unit 107, Winter Park

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park

$285,000

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan creates a flexible living space, and the thoughtful layout gives you a solid foundation to work with. Inside, the cathedral ceiling in the main living area draws the eye upward and enhances the sense of openness throughout the home. The covered rear lanai extends your entertaining and living space outdoors, perfect for relaxation or gatherings. The location delivers great convenience, with proximity to Publix-anchored shopping and Walmart for everyday needs, Red Bug Lake for outdoor recreation activities, grade schools, and the Winter Park Village for shopping and dining. Schools are nearby, making this neighborhood accessible for residents. The central location means you're less than 30 minutes from Orlando International Airport, Universal, Downtown Orlando, and UCF, offering both lifestyle flexibility and strong rental demand drivers for those considering income-producing use. Convenient access to major roadways makes commuting and daily needs straightforward. Schedule your private showing today and bring your vision for what this home can become.

7348 Grand Avenue, Winter Park

$659,000

3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code

POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, Winter Park

$1,599,000

4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park

$1,250,000

3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront. Option 2 — $1,450,000 155' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

$2,400,000

Killarney Estates SubDv. ⋅ 32789 Zip Code

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY! .39 acres: 17,100 sq ft (approx 24,000 sq ft: .55 acres including lakefront & street easement on both corner streets: 95 ft lakefront not included in FAR) Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead-end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE Optional OPPORTUNITIES: Option 1 — $1,450,000 155' x 65' property + 65' lakefront. Option 2 — $1,250,000 115' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

4572 N Palmetto Avenue Unit A, Winter Park

$3,200,000

4572 Palmetto Condo SubDv. ⋅ 32792 Zip Code

Prime commercial/industrial opportunity in Winter Park! This warehouse building offers excellent visibility and exposure along high-traffic Palmetto Ave., also known as Goldenrod Road, with approximately 275+ feet of road frontage. The property is zoned Industrial and features approximately 11,500 square feet of total space, including warehouse, showroom, office, and retail/wholesale areas. Warehouse: Approximately 8,000 sq. ft. featuring:3 overhead doors, High loading dock, Exhaust fans & Mezzanine. Showroom / Wholesale & Retail: Approximately 8,843 sq. ft. of air-conditioned space, featuring:2 private offices, 3 full bathrooms, Full kitchen. This property offers a versatile layout and excellent visibility for a variety of industrial, wholesale, retail, and commercial uses. SELLING BUILDING ONLY. Business, inventory, furniture, automobiles, equipment, and other personal property do not convey with the sale.

4572 N Palmetto Avenue Unit A, Winter Park

$594,000

4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code

RENOVATED 4 BED / 3.5 BATH TWO-STORY | GOURMET KITCHEN | LUXURY VINYL FLOORING | ROOF 2018 | FENCED BACKYARD | CLOSE TO ALOMA AVE & SR 417 Welcome to 4260 Bear Gully Road, a beautifully updated, move-in-ready home for anyone who wants a truly nice place to live. The heart of the home is the gourmet kitchen, fully remodeled just two years ago with upscale cabinetry and modern appliances, perfect for everyday meals and entertaining. Luxury vinyl flooring gives the home a clean, modern look that is easy to maintain. With four bedrooms and four full bathrooms across two stories, everyone has room and privacy, whether for family, guests or a home office. Enjoy the screened lanai and the fenced backyard, ready for pets, play and weekend get-togethers. Added peace of mind: roof replaced in 2018, concrete block and stucco construction, and Flood Zone X. Location is a major plus. You're near the Publix-anchored shopping, dining and services along Aloma Avenue, AdventHealth Winter Park, and the Cross Seminole Trail, with easy access to SR 417 (Central Florida GreeneWay). Winter Park Village and the boutiques and restaurants of Park Avenue are a short drive away. Served by Seminole County Public Schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!

4260 Bear Gully Road, Winter Park

$3,545,995

4 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

The Art of Living Well: A New Chapter at "Moon Haus" Winterpark From the moment the custom 10-foot glass pivot door swings open, you realize this is not just a house—it is the life you have been envisioning. Designed and built as a true ground-up architectural revival, this residence delivers the pristine caliber, modern engineering, and turn-key experience of brand-new luxury construction. You step into the light-flooded foyer, and the outside world instantly quietens. Your eyes trace the subtle, warm grain of sleek Italian wood underfoot, drawing you effortlessly into a space crafted for both quiet contemplation and grand celebrations. Standing in the main living room, anchored by a dramatic statement fireplace, you can already picture it: crisp mornings spent with espresso in hand as gentle light filters through, and vibrant evenings filled with laughter as friends gather around. Every moment here feels orchestrated for ease. With a subtle tap, the home awakens around you. Music softly fills the air, lighting shifts to set a relaxed evening mood, and the climate adjusts seamlessly through the integrated Control4 system—an invisible concierge catering to your every preference. Moving into the kitchen, the space invites you to create. Light-toned European cabinetry conceals clever storage, while striking Neolith double countertops frame professional-grade Sub-Zero and Wolf appliances. It is a masterclass in culinary sophistication, whether you are hosting an intimate multi-course dinner party or savoring a slow, sun-drenched Sunday morning. When it is time to unwind, the home transitions into a private resort. You slide open the glass doors and step out onto the rich Brazilian IPE wood deck. The French gray mini-pebble pool glimmers ahead, warmed to perfection. At dusk, you fire up the sintered-stone summer kitchen under the Florida stars, preparing a meal al-fresco while the soft exterior lighting paints the lush, manicured grounds. At the end of the day, retreat to your en suite sanctuary. Each bedroom offers a secluded escape, but the primary suite feels like an exclusive boutique hotel. You step into the spa-inspired bath, surrounded by custom vanities, Neolith surfaces, and gentle ambient lighting, feeling a profound sense of calm. Set within one of Winter Park’s most coveted enclaves, just moments from the energy of Park Avenue, the prestigious Interlachen Country Club, and Phelps Park, this residence offers the rare opportunity to own a virtually new masterpiece in an established, iconic location. Experience the art of living well—connect with us today for an exclusive private tour!

1742 Temple Drive, Winter Park

1306 S Pennsylvania Avenue Unit 5, Winter Park

$349,000

2 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code

NEW PRICE! Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

1306 S Pennsylvania Avenue Unit 5, Winter Park

7453 Daniel Webster Drive Unit A5, Winter Park

$150,000

2 Beds ⋅ 2 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in Winter Park. The home features a newer HVAC system installed in 2021, repiped plumbing completed in 2021, and a new electrical panel installed in 2021. One bedroom provides direct access to the patio, offering convenient outdoor space. The property is conveniently located near UCF, shopping, dining, major roadways, Downtown Orlando, and Orlando International Airport. An excellent opportunity to own a well-maintained condo in a convenient Central Florida location.

7453 Daniel Webster Drive Unit A5, Winter Park

$2,095,000

4 Beds ⋅ 4 Baths ⋅ Lake Virgina Shores SubDv. ⋅ 32789 Zip Code

Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre with deeded access to Lake Virginia. Impeccably maintained, the 4-bedroom, 4-bath home offers 3,776 square feet of heated living space, including an office and sunroom. Inside, a welcoming foyer opens to a traditional floor plan with large formal living and dining rooms on either side. Straight ahead, the spacious family room with fireplace flows into the kitchen, where new quartz countertops and backsplash, upgraded appliances, and gorgeous travertine floors make this a true chef's kitchen. Beyond the kitchen, a light and bright sunroom looks out over the inviting pool and patio with outdoor kitchen. The downstairs office could easily be converted to a first-floor bedroom with an adjacent full bath. Upstairs, you'll find a large primary suite and three additional bedrooms. One of the home's most inviting features is the expansive upper balcony stretching the length of the house and overlooking the pool, perfect for entertaining or enjoying a quiet evening outdoors. Recent updates include a newly renovated kitchen, 2017 roof, and newly reimagined landscaping. Zoned for Audubon Park K-8 and Winter Park High School, and close to Winter Park's historic restaurant and shopping district, this is the perfect location to enjoy everything the area has to offer.

555 E Lake Sue Avenue, Winter Park

$1,049,000

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

2463 Grand Teton Circle Unit 2463, Winter Park

$249,000

3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park

$2,190,000

4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park

$299,900

3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code

FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park

250 Carolina Avenue Unit 202, Winter Park

$649,000

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park

$469,900

3 Beds ⋅ 2 Baths ⋅ Winter Park Forest SubDv. ⋅ 32792 Zip Code

This beautifully transformed 3-bedroom, 2-bathroom block home offering modern updates, quality finishes, and true move-in-ready appeal in Winter Park. This standout property features a 2-car garage, spacious 3-bedroom layout, and an extensive renovation completed with today’s buyer in mind. Step inside to a bright, redesigned open-concept kitchen with a fresh, modern feel, brand new kitchen appliances, range with oven, microwave, complemented by brand-new flooring throughout and two completely renovated bathrooms. Major improvements include a new 2026 A/C system, new windows, fresh interior and exterior paint, along with an extensive list of additional upgrades throughout the home. Thoughtfully renovated, beautifully presented, and ready for its next owner—this is a home you’ll want to see in person to fully appreciate.

3334 Young Street, Winter Park

$899,900

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

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