Winter Park Real Estate

Winter Park Real Estate

Welcome to Winter Park, Florida – a picturesque gem nestled just north of Orlando, known for its charming streets, vibrant culture, and stunning natural beauty. This enchanting city seamlessly blends small-town charm with modern amenities, making it an ideal destination for families, retirees, and everyone in between.

Winter Park is renowned for its lush landscapes, featuring beautiful parks, scenic lakes, and tree-lined boulevards. The crown jewel, Central Park, offers a serene escape where residents and visitors can enjoy leisurely strolls, picnics, and community events. The city is also home to the stunning Chain of Lakes, perfect for boating, fishing, and enjoying breathtaking sunsets.

Art and culture thrive in Winter Park, with the renowned Morse Museum of American Art showcasing an impressive collection of Tiffany glass. The city also hosts various art festivals and cultural events throughout the year, celebrating local talent and creativity. Stroll along Park Avenue, where you’ll find an array of boutique shops, charming cafes, and delectable dining options, making it the perfect spot for a leisurely afternoon.

For those who appreciate a vibrant community, Winter Park offers a variety of activities and events, from farmers' markets to outdoor concerts. The city's strong sense of community and commitment to preserving its historic charm make it a truly special place to call home.

With its unique blend of culture, nature, and a welcoming atmosphere, Winter Park is not just a place to live; it's a lifestyle. Discover your dream home in this captivating city and experience all that Winter Park has to offer!

Newest Listings in 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
2052 Wood Thrush Lane, 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
200 Saint Andrews Boulevard Unit 3408, Winter Park
$170,000
1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
Great opportunity to own or invest in a 1 bedroom, 1 bath, second floor condo in the highly sought after Four Seasons community of Winter Park. The entire unit has just been newly painted, includes stackable washer and dryer and a newly painted screened porch with a storage closet facing the lushly landscaped courtyard. The community offers three community pools, tennis courts, car wash area and multiple laundry facilities. Conveniently located to restaurants, Winter Park Hospital and grocery stores. Easy access to Park Avenue and close proximity to Rollins, Full Sail and UCF.

200 Saint Andrews Boulevard Unit 3408, Winter Park
918 Enclave Place, Winter Park
$2,125,000
5 Beds ⋅ 5 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Pre-Construction. To be built. Introducing 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
170 Balfour Drive Unit 1, Winter Park
$299,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pointe 01 SubDv. ⋅ 32792 Zip Code
RARELY AVAILABLE CORNER VILLA IN A PRIVATE, SERENE SETTING! Welcome to this beautifully remodeled Winter Park villa, tucked away on a private drive and offering the exceptional privacy and charm of a coveted corner location. From the moment you arrive, the inviting front courtyard sets the tone for a home that feels both elegant and effortlessly comfortable. This residence offers a fresh, elegant feel throughout, including a beautifully updated kitchen, bedrooms, lighting, plumbing, appliances, and more. The home has been remodeled with attention to both style and everyday living. A recently renovated Mediterranean-style tile roof, completed in March 2026, adds timeless architectural character while providing peace of mind for years to come. The indoor-outdoor living experience is equally appealing, with a lovely private rear patio creating the perfect setting for entertaining or simply unwinding at the end of the day. A spacious attached two-car garage provides exceptional convenience and plenty of storage space. And for everyday ease, you even have your own private mailbox attached directly to the home. One of the things that makes this villa especially appealing is the peace of mind that comes with the HOA. If you’re looking for a true lock-and-go lifestyle, the HOA takes care of the exterior maintenance, beautiful landscaping, pest control, and more, so you can simply come home, relax, and enjoy it without worrying about the upkeep. Ideally situated near all that makes Winter Park so desirable, this home places you just minutes from the charm of Park Avenue, where boutique shopping, celebrated dining, cafés, arts, culture, and leisurely strolls come together in one of Central Florida’s most beloved destinations. This is a rare opportunity to enjoy a turnkey villa with character, comfort, privacy, and an enviable location—a home that lets you spend more time enjoying where you live and less time taking care of it. Call for your private showing today!

170 Balfour Drive Unit 1, Winter Park
1409 Aster Court, Winter Park
$589,900
4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to 1409 Aster Court, a fully refreshed single-story home in Garden Lake Estates, where Winter Park’s address meets the quiet of Seminole County. No HOA. No monthly dues. Just a private, fenced backyard, a screened pool, and the kind of established street where the loudest thing most evenings is the breeze through the palms. From the concrete pavers walkway, fieldstone columns and a James Hardie board and batten gable frame a modern entry and a two-car garage. Inside, the renovation is the story. Light luxury vinyl runs through an open living area that flows straight to the kitchen: shaker cabinets, matte hardware, speckled quartz counters, and stainless appliances, including a French-door refrigerator. A warm wood-slat accent wall gives the great room a finished, designer feel without making the space feel small. The primary suite is set up for real everyday living, with a wood vanity, dual sinks, a backlit mirror, and a marble-look walk-in shower. A second bath carries the same updated finishes, glass enclosure, and rainfall shower. Bedrooms are light and flexible, one with a barn door and a wood-blade fan, another in a soft sage that already feels move-in ready. Out back, the screened pool cage opens to a generous yard — room for morning coffee, weekend swims, and the kind of privacy that is hard to find this close to everything. Garden Lake Estates is a settled, low-key pocket of larger lots and mature trees, with the community lake nearby and none of the restrictions that come with a managed association. Seminole County schools are a major draw here; buyers should confirm the exact zone for this address. Winter Park dining, Park Avenue, and the chain of lakes are a short drive. Oviedo, Casselberry, and the 417 and 434 corridors keep commuting practical. If you have been looking for an updated pool home, a quiet street, and the freedom of no HOA in a strong Seminole County school area, this is the one to walk through.

1409 Aster Court, Winter Park
1871 Bryan Avenue, Winter Park
$599,000
Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Opportunity meets location at 1871 Bryan Avenue in highly sought-after Winter Park 32789. Set on a 50-by-127-foot lot, this property offers an appealing opportunity for builders, investors, or buyers looking to create a custom home or pursue a new construction project in an established neighborhood. The location places you just minutes from Park Avenue, Winter Park Village, dining, shopping, and everyday conveniences, making it an attractive setting for both future homeowners and investment-minded buyers. With its manageable lot size, central location, and long-term potential, this property provides a compelling opportunity to build and invest in one of Central Florida’s most desirable markets.

1871 Bryan Avenue, 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
2139 Blossom Lane, Winter Park
$699,000
32789 Zip Code
Rare opportunity to build your custom waterfront home in the heart of Winter Park's 32789. This cleared, ready-to-build lot sits on a canal with boating access to Lake Killarney, one of the area's most sought-after ski lakes. Spend your days skiing and cruising, then boat up to the dock at Hillstone Restaurant for lunch or dinner with sunset views over the water. All this comes with the convenience and prestige of a Winter Park address, just minutes from Park Avenue, dining, and shopping. Some photos have been virtually staged.

2139 Blossom Lane, Winter Park
3150 Shady Pine Avenue, Winter Park
$439,900
4 Beds ⋅ 2 Baths ⋅ Bel Aire SubDv. ⋅ 32792 Zip Code
MOVE-IN READY with a spectacular LAP POOL! Nestled in the desirable Bel Aire Pines community of Winter Park, this beautifully maintained 4-bedroom, 2-bath home offers an exceptional combination of comfortable living, valuable updates, and fantastic outdoor space—all with NO HOA! Step inside to a bright and inviting floor plan featuring formal living and dining rooms, along with a spacious kitchen appointed with granite countertops, upgraded cabinetry, and a charming dinette area for casual meals. The spacious primary suite offers a private ensuite bath with a walk-in shower and built-in seating, granite counter, mirrored medicine cabinets, and beautiful cabinetry. Three additional bedrooms provide plenty of space for family, guests, a home office, or hobby room. The elegant upgraded hall bath features granite counter, spacious mirrored medicine cabinets, and a tub/shower combination with neutral tile and Listello accent. Step outside to discover one of this home's standout features—a fabulous 17' x 50' lap pool, perfect for swimming and exercise, cooling off on warm Florida days, or hosting fun gatherings with family and friends! A screened rear patio provides additional space to relax and entertain while overlooking the pool and private backyard framed by attractive white vinyl fencing. The home has been thoughtfully maintained with important improvements including replumbing (2024), water heater (2026), electrical panel (2023), HVAC system (2023), Energy Star Qualified windows (2023), garage door (2022), and roof (2017)—valuable updates that add comfort and peace of mind. Additional features include carpet, tile and bamboo flooring, water softener, attic fan, and a washer and dryer in the garage. ALL APPLIANCES, INCLUDING THE WASHER AND DRYER, ARE INCLUDED! Ideally situated in Winter Park with convenient access to shopping, dining, Full Sail University, UCF, schools, major roadways, and everyday conveniences, this move-in-ready home offers the space, updates, location, and incredible pool you've been looking for. Schedule your private showing today!

3150 Shady Pine Avenue, Winter Park
2500 Lee Road Unit 123, 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
188 Sandlewood Unit 1, 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
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