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$739,000
4 Beds ⋅ 4 Baths ⋅ Quesinberry Sub SubDv. ⋅ 34787 Zip Code
Duplex home in Downtown Winter Garden! 3 bedroom and 2 bathrooms on each side with a total of 6 bedrooms and 4 bathrooms. One block from Plant street in Winter Garden!

209 S Boyd Street, Winter Garden
$739,000
4 Beds ⋅ 4 Baths ⋅ Quesinberry Sub SubDv. ⋅ 34787 Zip Code
Duplex home in Downtown Winter Garden! 3 bedroom and 2 bathrooms on each side with a total of 6 bedrooms and 4 bathrooms. One block from Plant street in Winter Garden!

208 S Main Street, Winter Garden
$739,000
6 Beds ⋅ 4 Baths ⋅ Quesinberry Sub SubDv. ⋅ 34787 Zip Code
Duplex home in Downtown Winter Garden! 3 bedroom and 2 bathrooms on each side with a total of 6 bedrooms and 4 bathrooms. One block from Plant street in Winter Garden!

215 S Boyd Street, Winter Garden
$739,000
4 Beds ⋅ 4 Baths ⋅ Quesinberry Sub SubDv. ⋅ 34787 Zip Code
Duplex home in Downtown Winter Garden! 3 bedroom and 2 bathrooms on each side with a total of 6 bedrooms and 4 bathrooms. One block from Plant street in Winter Garden!

214 S Main Street, Winter Garden
$450,000
3 Beds ⋅ 1 Baths ⋅ Millers Pt Winter Garden SubDv. ⋅ 34787 Zip Code
Located in downtown Winter Garden! Three bedroom and 1 bathroom home with one car carport.

85 N Boyd Street, Winter Garden
$289,000
2 Beds ⋅ 1 Baths ⋅ Shadow Lawn SubDv. ⋅ 34787 Zip Code
This beautiful remodeled home in downtown Winter Garden is waiting just for you! Experience the perfect combination of convenience, charm, and peace of mind in this wonderfully maintained 2-bedroom, 1-bath home, offering 836 sq. ft. of thoughtfully designed living space, just a 10-minute walk to vibrant downtown. Step inside to find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinetry, perfect for everyday meals or entertaining friends. The bright and inviting interior is complemented by an enclosed back porch, ideal for morning coffee or relaxing with a good book. The fully fenced backyard with lighting creates the perfect setting for evening gatherings, weekend barbecues, or quiet outdoor enjoyment. Outside, the freshly painted exterior and new landscaping add exceptional curb appeal. A garage with electric and a refrigerator, plus a covered parking spot, ensures both convenience and extra storage. This home isn’t just move-in ready, it’s worry-free! The roof, plumbing, and electrical systems were professionally inspected in July 2025 and are all in great condition, and a termite bond with Massey adds even more security. Additional updates like central air and new windows (2010) make this home efficient and comfortable year-round. Best of all, you’re just steps away from downtown’s farmers markets, community festivals, live music events, and local dining. Spend your weekends exploring boutique shops, enjoying outdoor markets, or connecting with neighbors at one of the many community events, all within a short walk from your front door. Located close to amazing schools, major highways and less than 30 minutes from Central Florida's top attractions like Disney World and Universal Studios, you can enjoy that small town charm while being close to all the fun Central Florida has to provide. If you’ve been searching for a home that offers modern upgrades, low-maintenance living, and an unbeatable location, this is the one. Don't wait on this gorgeous home, schedule your private showing TODAY!!!

215 Pennsylvania Avenue, Winter Garden
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code
Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural zoning designation). Very quiet. Very private. No HOA and close to Winter Garden and Windermere amenities as well as all theme parks.

13377 Lake Butler Boulevard, Winter Garden
$120,000
1 Beds ⋅ 1 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. --$100K Renovation just completed, Winter Garden Gem, unlike any other condo in the community! Welcome to your dream studio condo in the charming Townhomes of Winter Garden—where everything is brand new, from the floor joists & spray insulation to the ceiling! This fully renovated single-story end-unit is tucked away at the end of a quaint cul-de-sac and has never been lived in since the transformation was completed. Step inside and be wowed by the thoughtful redesign and modern upgrades throughout. What’s new? Just about everything! Enjoy new flooring, new roof, new plumbing, new electrical, fresh new walls, new textured ceilings with recessed lighting & a sleek ceiling fan, and energy-efficient windows. The brand new split HVAC system and updated electrical panel provide year-round comfort and peace of mind. The kitchen is a standout feature, redesigned with all-new stylish cabinetry featuring soft-close drawers and doors, new stone counters, a new black and stainless steel dishwasher, a deep sink, and a new range installed in late 2024. The black refrigerator, just a few years old, completes the modern look with a coordinated and functional design, perfect for everyday living and entertaining. The bathroom has been beautifully reimagined with a spacious walk-in tiled shower, stone-topped vanity, and contemporary finishes. Additional upgrades include a new laundry area with a washer and dryer replaced just a few years ago, a bonus storage closet, new exterior stucco, a new front door with an electronic lock, and more. Enjoy assigned parking and relax at the community pool, all just minutes from everything downtown Winter Garden has to offer—including Crooked Can Brewery, local dining, boutique shopping, farmers markets, and live entertainment. This is your chance to own a completely turnkey, never-lived-in condo in one of Central Florida’s most sought-after communities!

416 Eron Way Unit 30, Winter Garden
$797,678
5 Beds ⋅ 5 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code
Sold Data Only

13129 Faro Court, Winter Garden
$1,157,300
5 Beds ⋅ 5 Baths ⋅ Lake Star/Ovation Ph 1a SubDv. ⋅ 34787 Zip Code
The Manor Series single family homes at Lake Star at Ovation were thoughtfully designed with flex spaces and open-concept floorplans for growing families. Some of our Manor homes will also be available on 60' lakefront lots!This plan includes 5 bedrooms, 4.5 bathrooms, and a 3-car garage.

17456 Glossy Pomelo Way, Winter Garden
$1,550,000
4 Beds ⋅ 5 Baths ⋅ Showalter Park SubDv. ⋅ 34787 Zip Code
Welcome to your dream home in the heart of Winter Garden's Golf cart Community! This stunning 4 bedroom 4.5 baths residence offers a perfect blend of luxury and comfort, ideal for families and entertaining. This home features: Spacious Layout: Enjoy an expansive open floor plan that seamlessly connects the living, dining, and Kitchen area, perfect for gatherings and family activities. Game room: The dedicated game room provides a fun space for entertainment, ensuring everyone has a place to unwind and enjoy. The office/ 5th bedroom. Outdoor living: Charming porch with summer kitchen, equipped with roll-up screens, creating an inviting outdoor space that can be enjoyed year-round. With high-end appliance and a gas cooktop. The home has 1 laundry room with butler's pantry. 1 laundry room upstairs. Ton's of storage. Don't miss the opportunity to own this exquisite home that combines luxury living with welcoming community.

284 Donald Drive, Winter Garden
$466,990
4 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Brand new townhouse. Amazing finishing. Ready to move in. Lots of parking space.

6352 Tabebuia Parkway, Winter Garden
$770,000
3 Beds ⋅ 2 Baths ⋅ Annie L Berry Sub SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom ranch-style home, ideally located within a 6-minute walk to historic downtown Winter Garden in the heart of the Golf Cart District. Situated on a spacious corner lot, this home blends classic charm, thoughtful upgrades, and everyday functionality—perfect for families, snowbirds, or anyone seeking a relaxed yet connected lifestyle. Step inside to an open and airy floor plan featuring wood flooring in the main living areas and tile in the kitchen and bathrooms. The generously sized kitchen serves as the heart of the home, offering abundant counter space, ample storage, and natural light—ideal for cooking, entertaining, or casual dining. The fully fenced backyard provides privacy and space for outdoor living, pets, or play. A rare find, the 2-car garage includes a pass-through rear door that opens to an additional parking pad—perfect for a trailer, golf cart, or extra vehicle. You’ll also find a small air-conditioned room inside the garage, ideal for a home office, workout space, hobby room, or climate-controlled storage. Located in one of Winter Garden’s most desirable areas, you’re just a quick golf cart ride from local shops, restaurants, the farmers market, and community events. With no HOA and a layout built for both comfort and convenience, this home offers a unique opportunity to enjoy both peace and a vibrant, walkable lifestyle.

205 S Woodland Street, Winter Garden
$417,000
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks At Hamlin Phase 3a 115/63 Lot 415 SubDv. ⋅ 34787 Zip Code
SOLD DATA ENTRY ONLY

6358 Tabebuia Parkway, Winter Garden
$860,000
4 Beds ⋅ 3 Baths ⋅ Encore At Ovation Phase 3 SubDv. ⋅ 34787 Zip Code
Beautiful resale property located in a well-established community. This home features spacious living areas and a practical layout. Recently sold in a private transaction with buyer and seller represented.

Winter Garden
$545,000
3 Beds ⋅ 3 Baths ⋅ Hamlin Pointe SubDv. ⋅ 34787 Zip Code
The Brantley floorplan is designed to impress, featuring 3 spacious bedrooms, 2.5 baths, and a versatile loft perfect for an office, child's playroom, or additional entertainment space. This home exudes a sense of spaciousness with 8-foot doors throughout, 10-foot ceilings, and an open stair railing. The gourmet kitchen, equipped with premium finishes and appliances, makes this home the perfect place to call your own. In addition, the detached garage adds both convenience and charm, with a courtyard, covered breezeway, and a covered lanai, offering plenty of space for relaxation or outdoor gatherings. This homesite backs to a dry pond, providing a serene view and even offers glimpses of the Disney fireworks from your windows, making it truly a magical place to call home. Located in the heart of Hamlin, this home is near Hamlin Middle and Hamlin Elementary, and just 5 minutes from the Hamlin Town Center, which offers grocery stores, restaurants, and more. It’s right up the road from Orlando Health Hospital, Orange County National Golf Course, and the soon-to-be Orlando Surf Park. Plus, you're only 10 minutes from Disney and so much more. This location truly offers the best of both convenience and luxury living!

16854 Hamlin Vista Alley, Winter Garden
$75,000
Black Lake SubDv. ⋅ 34787 Zip Code
Great Opportunity to purchase a completely cleared vacant lot in the heart of Winter Garden. This Corner Lot is already sitting on two separate lots (16 & 17) with one Parcel ID. Therefore, it should be allowed to split into two different Parcels with Orange County; officially making it two buildable lots. Surveyor said lot split should work and Buyers interested in splitting would need to do a Survey showing two different lots and request official lot split with Orange County on lots already separated. BIG PLUS!! Survey Available. Easy access right off Astrolyn Street where there is approximately 200 Ft. frontage. GREAT LOCATION just minutes from the amazing Downtown Winter Garden area that offers a number of original restaurants, shops and night life. Let's not forget the West Orange Trail, Kid's Splash Park and renown weekly Farmers Market. Literally take Avalon across Colonial and you RUN INTO Downtown Winter Garden. It's That Close! IN ADDITION there is an incredible recreation facility coming called the Tucker Ranch Wellness Park set to be built right up the street THIS YEAR! Look it up online - it's awesome and supposed to have community garden. In the meantime, this park is currently Tucker Ranch Recreation & Nature Facility that has playground, picnic tables, huge area to walk pets and hiking trail. All walking or biking distance from this lot. This property is located on street just off West Colonial with quick access to the 429, Turnpike, 408, 441 and I-4. Numerous shopping plazas and Orlando Health Hospital off 50 close by. Perfect time to buy this lot now before Tucker Ranch Wellness Park opens as home values in area will likely rise substantially once this Community Gem is complete. Please check internet for more information on this fabulous facility opening THIS YEAR that has partnered with West Orange Health District to build a state of the art Wellness Park. This will be a fabulous addition to the community! Feel free to drive by and check the property out while being respectful to neighbors. Lots of potential. Especially if you can make one lot into two! Nice small homes on Astrolyn next to this lot and vacant area across street could bring others.

14855 Astrolyn Street, Winter Garden
$278,000
2 Beds ⋅ 2 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code
Investor’s Dream Near Downtown Winter Garden – 1 Acre with Endless Possibilities! This concrete block 2 bed, 2 bath home sits on a spacious 1-acre lot just 5 minutes from charming and thriving Downtown Winter Garden. With a solid foundation and strong bones, this property is the perfect canvas for your next investment project. Whether you're looking to renovate and flip, add square footage, or build your portfolio with a long-term rental, the potential here is massive. Nestled among mature trees with no HOA, there’s plenty of room for expansion or even a future custom build. Opportunities like this—a full acre this close to Winter Garden's restaurants, shops, and weekly farmer’s market—are rare. Don’t miss the chance to turn this hidden gem into a high-performing asset! Schedule your showing today and envision what’s possible.

321 Beard Road, Winter Garden
$691,790
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Beautiful new construction home in the saught after Del Webb Oasis community.

15533 Orchid Rose Court, Winter Garden
$755,800
3 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Brand new house.

5314 Citrus Leaf Boulevard, Winter Garden
$405,000
4 Beds ⋅ 2 Baths ⋅ Garden Heights SubDv. ⋅ 34787 Zip Code
Sold off market

517 Garden Heights Drive, Winter Garden
$1,184,779
4 Beds ⋅ 3 Baths ⋅ Lake Star/Ovation-Ph 1a SubDv. ⋅ 34787 Zip Code
Short Sale. Hamlin Pointe stands out with its unique combination of dining, shopping, entertainment, and walkability, offering residents a lifestyle that caters to both leisure and daily needs. Embracing the essence of a flourishing neighborhood, Hamlin is not only a hub for diverse retail options but also boasts top-notch educational facilities and is surrounded by a thriving medical landscape. In Hamlin Pointe, you'll find a community that seamlessly integrates into the dynamic and evolving essence of Orlando's growth.

Winter Garden
$888,000
3 Beds ⋅ 3 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. ***NEW REDUCED PRICE!***MOVE IN BEFORE THE HOLIDAYS & TAKE ADVANTAGE OF THE LOWER INTEREST RATES! The sellers are motivated and ready for the next chapter—creating an incredible opportunity for you to own this beautifully updated Craftsman-style home on a rare .53-acre R-2 zoned lot in the heart of Downtown Winter Garden’s golf cart district. Offering character, comfort, and flexibility with no HOA, this property is move-in ready and waiting for your vision—whether that’s an addition, guest house, pool, or even a potential lot split (with city approval). Inside, over 2,200 sq. ft. of living space has been refreshed from top to bottom with thoughtful 2025 updates including a NEW ROOF, fresh interior paint, refinished original hardwood floors, new luxury vinyl plank flooring, new stainless steel French door refrigerator, updated lighting, and refinished rear deck with new railings, stairs, and stain. The floor plan offers multiple gathering spaces, including a spacious family room with wood-burning fireplace, and a custom kitchen equipped with stainless appliances, gas 6-burner cooktop, double ovens, and breakfast bar. The front sunroom provides a bright and versatile space—perfect for a home office, reading nook, or creative studio. Upstairs, the primary suite features hardwood flooring, a generous walk-in closet, and an inviting en-suite bath with a clawfoot tub and tiled shower. Downstairs are two additional bedrooms and a second full bath providing room for family or guests. Outdoor living shines here—enjoy a fully fenced backyard with three wood decks, established butterfly and vegetable gardens, and a 14,000-gallon above-ground pool (2020). The expansive 23x25 main deck is ideal for entertaining, grilling, or simply relaxing in your private oasis. Major system upgrades add even more value: dual HVAC systems (2019 & 2020), Rinnai tankless gas water heater (2023–24), updated electrical panels (2005 & 2020), termite tenting with transferable bond (2025), and an oversized 2-car garage with new openers (2023 & 2025). A charming enclosed breezeway with Saltillo tile flooring and tongue-and-groove ceiling (2025) connects the home to the garage and an attached storage building—perfect for hobbies or workshop space. Located just blocks from the West Orange Trail, Plant Street Market, the weekly Farmers Market, and all of Winter Garden’s award-winning restaurants, coffee shops, and boutiques, this home offers an unbeatable blend of lifestyle and location. The holiday season in Winter Garden is one of the most beautiful times of the year. This beautiful property is the perfect place to start the new year!

524 S Lakeview Avenue, Winter Garden
$429,900
3 Beds ⋅ 2 Baths ⋅ Garden Heights SubDv. ⋅ 34787 Zip Code
This well-maintained home features a split-bedroom design with comfortable living spaces and a practical floor plan that offers a versatile layout ready for daily living and any occasion. This property welcomes you with its warm curb appeal, featuring a stone and wood paneling exterior, with mature trees and no rear neighbors enhancing this peaceful escape. The home features a spacious living room with a wood-burning fireplace serving as the central gathering area, complemented by a generous screened patio that extends your living space while offering protection from the elements throughout the seasons. Three spacious bedrooms and two bathrooms make up the living quarters, providing everyone with their own piece of privacy. The new roof installed in 2019, and recent updates, including fresh interior and exterior paint, new luxury vinyl tile, new gutters, new ceiling fans, and serviced the HVAC System and fireplace to ensure peace of mind for years to come, while its location enjoys no HOA fee or restrictions, proximity to the Lake Apopka waterfront park, including a community pool, and the area allows golf carts for a swift ride to enjoy Downtown Winter Garden just 1.5 miles away. Convenient access to SR-429 and the FL-Turnpike allows for a straightforward commute or to easily explore all that Central Florida has to offer. The combination of indoor and outdoor living spaces, recent upgrades, and location makes this property well-suited for those desiring comfort and privacy, with great accessibility for daily living and exploring. Schedule your private showing today to experience this wonderful home firsthand!

525 Garden Heights Drive, Winter Garden
$476,090
4 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Welcome to the stunning Julep model home! This beautifully designed residence showcases the perfect blend of style, comfort, and functionality. Featuring an open-concept layout, designer finishes, and thoughtful upgrades throughout, the Julep model impresses with its spacious kitchen, elegant primary suite, and light-filled living areas ideal for both everyday living and entertaining. Located in a sought-after community, this home offered convenient access to parks, schools, and shopping while delivering the charm of modern Florida living.

6382 Tabebuia Parkway, Winter Garden
$448,590
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks At Hamlin SubDv. ⋅ 34787 Zip Code
Sold Data Only.

6343 Breeze Filled Lane, Winter Garden
$2,500,000
5 Beds ⋅ 6 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code
Welcome to your own private retreat in the heart of Downtown Winter Garden, just steps from the 22-mile West Orange Trail and nestled within the coveted Golf Cart District. This stunning single-story custom home offers the perfect blend of upscale living, natural beauty, and small-town charm. Set on an oversized fenced lot just under 1 acre, this turnkey estate features 5 bedrooms one with private entrance perfect for guest or in-law suite, 5 full en-suite bathrooms, 4,330 sq ft of thoughtfully designed living space, a resort-style pool with outdoor entertaining area, and an expansive 3-car garage with room to add an additional detached garage for all the toys. As you approach, you’re greeted by lush landscaping, rear privacy hedge, Magnolia Trees, and towering mature oak trees that provide shade and character throughout the property. Inside, this smart home is beautifully updated with high-end finishes, custom cabinetry, built in closet organizers, full home backup generator, sound system, security surveillance and an open-concept layout ideal for both everyday living and entertaining. The chef’s kitchen flows into a spacious family room with beautiful fireplace, and large windows that frame serene views of your backyard oasis. Step outside to enjoy the ultimate Florida outdoor living experience. The backyard is a showstopper—featuring a resort-style pool, outdoor kitchen with retractable screens, a cozy outdoor fireplace and living and dining area, and a dedicated fire pit area under the pergola, all designed for year-round entertaining and relaxation. Whether you’re hosting a party or enjoying a quiet evening under the stars, this home offers the perfect setting. This property is not only a sanctuary but also a gateway to one of Central Florida’s most vibrant communities. Just steps from Lakeview Middle School as well as West Orange Trail, you can walk, bike, or take your golf cart to Historic Downtown Winter Garden, where you’ll find award-winning restaurants, local breweries, coffee shops, live music, boutique shopping, the popular farmers market, and community events all year long. The lifestyle here is active, social, and completely unique. With No HOA enjoy the freedom to bring your RV, boat, or toys. This is a rare opportunity to own one of the area’s finest homes in a location that combines luxury, lifestyle, and unmatched community access. Schedule your private tour today and see why this incredible property is the best of Winter Garden living!

340 Lakeview Road, Winter Garden
$438,990
4 Beds ⋅ 3 Baths ⋅ . SubDv. ⋅ 34787 Zip Code
sold data entry only

6349 Breeze Filled Lane, Winter Garden
$490,000
4 Beds ⋅ 1 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Historic Craftsman in the highly desired Golf Cart zone of Downtown Winter Garden. Property has great bones but is in need of some updates. Perfect property for investors or buyers looking to design there dream home. House does have a New Roof 2024 and the AC is 2017. This is a rare opportunity with endless possibilities.

206 N Highland Avenue, Winter Garden
$2,700,000
Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
Probably the finest site for a huge estate home in Orange County! No need to move almost an hour away to Montverde just to find enough land to build your private estate or Equestrian estate when this gem is minutes to Windermere and everywhere you want to be. This highly sought after 10 acre property in the Lake Avalon rural settlement, is a declining citrus grove and sits on the highest elevation in West Orange County, which affords it incredible views in every direction. If you build a two story home on the property with a balcony situated just right, you can see all the way to Orlando, Windermere, and the nightly Walt Disney World fireworks. There is a contract in place for reclaimed water for irrigation and a clean well on the property for drinking water. This dream property is just minutes from the thriving downtown Winter Garden Village, Hamlin center, downtown Windermere and minutes to the 429 expressway to downtown Orlando, Disney, and all major shopping , dining, and attractions. This lot is a rare find! There is nothing like it on the market, and there never will be again, as quality parcels of country real estate are disappearing. Don't miss your chance to own your dream piece of country paradise!

17902 Seidner Road, Winter Garden