Location: Winter Garden , 34787
Do Not Show Listings
14501 GROVE RESORT AVE #2138, WINTER GARDEN, FL 34787
$190,00095 Days on yellowkey MLS ID: O6379849
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1396 Built: 2018Monthly Fee: $998 Tax: $8,154 (2024)Community: Grove Resort And Spa Hotel Condominium UCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,154
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Discover Exceptional Value at The Grove Resort & Water Park Orlando! This stunning 3-bedroom, 2-bath condo-hotel suite offers unbeatable value in one of Orlando's premier upscale resorts. Spanning a spacious 1,396 sq ft, this fully furnished, modern retreat is turnkey and rental-ready, complete with on-site professional management and a proven income-producing program. Step inside to find contemporary finishes, ample living space, and thoughtful details designed for comfort and convenience. You will appreciate the beautiful and easy to care for luxury vinyl plank flooring. All appliances are included. The modern fully equipped kitchen is ready for quick snacks or preparing a full gourmet meal. The resort's prime location places you just minutes from Walt Disney World®, Universal Orlando, SeaWorld, Margaritaville, movie theaters, and Orlando International Airport. Best of all, enjoy complimentary shuttle service to major theme parks. Resort highlights include the thrilling Surfari Water Park featuring a double FlowRider surf simulator, multiple pools, lazy river, waterslides, and family-friendly splash zones. Dine at on-site restaurants, relax by serene Lake Austin with its private pier—ideal for catch-and-release freshwater fishing (bass, bluegill, and more)—or explore the surrounding nature preserve. Whether you're seeking a dream family vacation spot or a smart investment property in Orlando's booming tourism market, this is your opportunity to own a piece of paradise. Schedule your private tour today and experience the magic of The Grove!
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Laura Block (321-229-6029)
12055 BRACCO ST, WINTER GARDEN, FL 34787
$429,000151 Days on yellowkey MLS ID: O6366675
3 Days Off yellowkey (back on 4/21/2026)
REDUCED by $11,000 (2.5%) on 04/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1668 Built: 2023Monthly Fee: $105 Tax: $6,881 (2024)Community: Highland RidgeSpa: NoSingle Family
Taxes:$6,881
Remarks: Under contract-accepting backup offers. Welcome to Your Florida Retreat! Step into a bright and breezy lifestyle in this seldom-offered home that captures the essence of Florida living year-round. Built in 2023, this well-maintained, energy-conscious single-family residence offers 3 bedrooms, 3 bathrooms, and approximately 1,668 sq ft of thoughtful living space on a 7,468 sq ft lot. Inside, enjoy a generous open-concept floor plan designed for comfort and ease — perfect for morning coffees, island-style dinners, or casual gatherings. The home features new lighting and energy-efficient windows to let in Florida sunshine while helping with energy savings. All bedrooms are upstairs, offering privacy and quiet; the attached garage adds convenience for everyday living. Outside, the property sits in a community that embodies that laid-back, sunny Florida vibe. Located in Winter Garden, FL, you’re just minutes from vibrant shopping, dining and entertainment options — from the historic charm of downtown Winter Garden and its weekend farmers’ market, boutiques, cafés, and arts scene to larger retail centers around Daniels Road and SR-429. For families or anyone valuing convenience, this home is within the public school zone of Water Spring Elementary School (PK-5), Water Spring Middle School-0482 (6-8), and Horizon High School (9-12) — all within a few miles of the home. Whether you’re relocating from out of state and seeking a home that offers easy maintenance, comfort, and solid investment value, or you’re a local buyer drawn to Winter Garden’s charm and amenities — this property combines practicality, modern updates, and that unmistakable Florida lifestyle.
Listing is courtesy of: POWERHOUSE REAL ESTATE NETWORK (305-409-6835)
Listing Agent: Luciana Figueiredo (781-635-2712)
604 FOSTER AVE, WINTER GARDEN, FL 34787
$400,00029 Days on yellowkey MLS ID: O6389095
0 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1975 Tax: $1,633 (2024)Community: Westchester PlaceSingle Family
Taxes:$1,633
Elementary School: Tildenville Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart District and directly across from Veterans Memorial Park, this property offers a lifestyle that blends convenience, privacy, and outdoor living. BRAND NEW ROOF JUST INSTALLED! (April 2026, 10-yr warranty) Set on a rare double lot, the home welcomes you with mature landscaping, an orchid tree in the front yard, stylish Bermuda hurricane shutters, and a covered front porch that provides a charming place to relax and enjoy the neighborhood. Inside, the spacious layout features durable porcelain wood-grain tile flooring installed in 2017, a bright living area, and a generous kitchen designed for everyday functionality and gathering. Major updates provide peace of mind, including all new double-pane windows installed in 2021, a water heater replaced in 2020, HVAC from 2019 (installed 2021) under warranty with American Air & Heat, and upgraded WiFi. Outside is where the property truly shines. The fully fenced backyard offers exceptional privacy with mature landscaping, fruit trees including kumquat, green apple, mango, and pineapple, along with bananas, plantains, pecan, and raised herb beds featuring aloe, basil, spearmint, and Italian oregano. Entertain or unwind on the recently resealed paver patio or under the pergola, while the powered shed with custom shelving and ramp provides flexible space for hobbies or storage. Additional features include a large private driveway, gutters, double weather-stripped front doors, and a chicken coop. With extensive updates, functional living space, and a backyard designed for gardening, relaxing, and entertaining, this home offers a unique opportunity to enjoy both comfort and outdoor lifestyle.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jackie Isham (407-917-8954)
7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787
$1,246,000291 Days on yellowkey MLS ID: O6329696
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3347 Built: 2014Monthly Fee: $195 Tax: $552 (2024)Community: Signature Lakes Parcel 1DSpa: YesSingle Family
Taxes:$552
Elementary School: Independence Elementary
High School: Horizon High School
Middle School: Bridgewater Middle
Remarks: SELLER MOTIVATED! Seller is offering a concession of up to $10,000 toward Buyer Pre-paids and Closing costs. Welcome to your dream oasis! This stunning 5-bedroom, 3.5-bath single-family home on Lake Hancock is a true masterpiece, offering the ultimate in luxury and comfort. With a contemporary design and exceptional features, this residence is a rare gem in the world of real estate. Upon entering this exquisite residence, you'll find a spacious living room and an elegant dining room, both thoughtfully designed for special occasions and entertaining. Continuing through the home, you'll be greeted by an exquisite open floor plan that seamlessly connects the kitchen, complete with top-of-the-line appliances, to the inviting family room. This perfect layout ensures that you're never far from the action, whether you're preparing a gourmet meal or enjoying quality time with family and friends. Natural light pours in through retractable sliding doors, creating an indoor-outdoor experience like no other. These doors lead to a captivating saltwater infinity pool and spa, perfect for relaxing on warm days or entertaining under the stars. With five generously sized bedrooms, there's plenty of space for your family and guests. The master suite is a sanctuary, featuring a spacious walk-in closet and an ensuite bath with all the luxurious amenities you deserve. Situated on a large corner lot, the property offers privacy and ample outdoor space for gardening, play, or simply basking in the sun. Your options are endless when it comes to creating your own outdoor paradise. This residence is not just a home; it's a lifestyle. Experience the epitome of elegance and modern living in every corner of this property. This home is just minutes from top-rated schools, shopping, dining, and moments away from the enchantment of Disney and Orlando's premier attractions.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Michele Acosta Gladding (407-963-6431)
16632 POINT ROCK DR, WINTER GARDEN, FL 34787
$550,000132 Days on yellowkey MLS ID: OM715702
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2292 Built: 2023Monthly Fee: $281 Tax: $8,546 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$8,546
Remarks: Short Sale. Located in the sought-after resort-style community of Waterleigh in Winter Garden, this spacious 2-story home features 4 bedrooms, 3.5 baths, and a versatile bonus room that can serve as a home office or additional bedroom. The first floor offers a guest bedroom with a full bath, a half bath, and an open-concept kitchen that flows into the living and dining areas—ideal for entertaining. Enjoy a fenced-in patio and a generous 2-car garage. Upstairs includes three more bedrooms, two full baths, and a family room. Enjoy access to community pools, clubhouse, fitness center, and more—just minutes from major highways and world-renowned attractions like Disney.
Listing is courtesy of: REMAX/PREMIER REALTY (352-732-3222)
Listing Agent: Melissa Lebron (352-304-1084)
9940 BLACK BEAR LN, WINTER GARDEN, FL 34787
$2,050,000359 Days on yellowkey MLS ID: O6309917
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3110 Built: 2025 Tax: $4,423 (2024)Community: Acreage & UnrecSingle Family
Taxes:$4,423
Remarks: Pre-Construction. To be built. This Custom Single-Story Modern Farmhouse by Lionshead Homes is a showstopper! Set on a serene 5-acre private oasis. Plenty of space for farm animals or just enjoy the open space and tranquil surroundings. Lionshead Homes has recently built custom homes near this property. So Buyers may view a recently completed home to get an idea of fit and finish and our quality craftmanship. Located in the Avalon Rural Settlement, you'll enjoy the country lifestyle without sacrificing proximity to shopping, entertainment and the suburban lifestyle of Hamlin and Winter Garden. Call for more information or to schedule a viewing appointment.
Listing is courtesy of: HAMLIN REALTY (321-299-4279)
Listing Agent: Edward Guerrette Llc (321-299-4279)
303 SOUTHERN P CIR #102, WINTER GARDEN, FL 34787
$228,00080 Days on yellowkey MLS ID: O6383580
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 838 Built: 2005 Tax: $2,540 (2024)Community: Southern Pines CondoCondo
Taxes:$2,540
Remarks: Welcome to the lifestyle you deserve in Winter Garden! This beautiful 1-bedroom, 1-bath condo in Southern Pines offers comfort, convenience, and resort-style living in a prime location. Enjoy outstanding community amenities including a spectacular pool, fully equipped fitness center, tennis courts, basketball court, BBQ area, playground, and expansive green spaces—perfect for relaxing or staying active. Ideally located just minutes from Historic Downtown Winter Garden and its popular shops, dining, and local markets, plus easy access to major highways like SR-429, making commuting and daily errands a breeze. With gated entry and a peaceful setting, this is the perfect place to call home—schedule your showing today!
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Fernando Villamizar Sarmiento (786-381-7469)
12373 BRACCO ST #12373, WINTER GARDEN, FL 34787
$500,000177 Days on yellowkey MLS ID: O6360606
2 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2003 Built: 2023Monthly Fee: $105 Tax: $7,593 (2024)Community: Highland RidgeSingle Family
Taxes:$7,593
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Beautiful, nearly new home located in the highly sought-after Highland Ridge community. This stunning property is situated on a quiet cul-de-sac and offers complete privacy with no neighbors in the back, providing a peaceful and serene environment. The home features premium finishes throughout, including custom California Closets in multiple bedrooms, built-in shelving, epoxy flooring in the garage, and premium light fixtures. It also comes equipped with high-end Hunter Douglas blinds/blackouts throughout, enhancing both comfort and style. In addition to the 4 bedrooms, the home offers a versatile flex room — perfect for an office, playroom, gym, or additional living space. The open-concept layout provides spacious living areas that flow seamlessly into a modern, contemporary kitchen, ideal for entertaining or everyday family life. The home comes move-in ready and includes a washer and dryer. Impeccably maintained, it combines elegance, functionality, and thoughtful design. A must-see property that will not last long!
Listing is courtesy of: POINTON REALTY INC (407-395-2860)
Listing Agent: Andrea Pointon (407-446-4414)
6408 FLAT LEMON DR, WINTER GARDEN, FL 34787
$550,00033 Days on yellowkey MLS ID: O6396757
REDUCED by $20,000 (3.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 2019Monthly Fee: $142 Tax: $8,155 (2025)Community: Hamlin ReserveSingle Family
Taxes:$8,155
Tax Year: 2025
Remarks: Tucked inside Hamlin Reserve in the heart of Horizon West, this beautifully maintained one-story home offers the kind of lifestyle buyers are looking for: modern, low-maintenance, and close to everything. Built in 2019 and still feeling like new, this 3-bedroom, 2-bath home with 1,979 heated square feet blends comfort, function, and thoughtful upgrades in all the right ways. From the moment you step inside, the open layout feels bright, welcoming, and easy to live in. Hardwood Laminate flooring runs throughout the entire home, including the bathrooms, creating a clean and cohesive look. The flexible dining room offers extra versatility and could easily become a private office, playroom, or enclosed flex space with French doors. The backyard is set up to be enjoyed, with a fully fenced yard ideal for pets, plus a built-in patio deck and firepit that make it easy to picture cozy evenings outside, weekend gatherings, or quiet mornings at home. Solar panels help drastically reduce the monthly electric bill, and the sellers will pay them off at closing, giving the next owner an added benefit from day one. Living in Hamlin Reserve means enjoying a community pool and being just minutes from the 429, Disney, shopping, grocery stores, dining, and all the energy and convenience that make Horizon West one of Central Florida’s most desirable places to call home. With no CDD, a move-in ready condition, and a location that continues to grow, this home is an ideal fit for buyers looking for both lifestyle and value. SAVE BIG: 1% Broker credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred broker.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Clementine Costantini (407-692-5453)
87 WINDTREE LN #K, WINTER GARDEN, FL 34787
$205,00072 Days on yellowkey MLS ID: G5108773
REDUCED by $15,000 (6.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1984Monthly Fee: $300 Tax: $587 (2024)Community: Windtree Gardens Condo Ph 03Condo
Taxes:$587
Elementary School: Maxey Elem
Remarks: Large Price Improvement. Downstair location, peace and ease with this updated 2/2 FIRST FLOOR condo in Winter Garden. You will love this condo placement in the rear of the community near the pond with fountain, community pool, rentable clubhouse, basketball courts and NO STAIRS. Enjoy the private setting while sitting on your screened porch with your favorite book or beverage and the frequent visits from the neighborhood ducks. The condo has been updated to include the cabinets, counters, updated bathrooms and tile floors throughout. Move in ready so just grab your things and come on. What's Nearby? ANYTHING you could need or want. Only 1.5 miles from downtown Winter Garden, 2.5 miles to Winter Garden Village, 15 miles to Walt Disney World® and other theme parks, 24 miles to MCO Orlando's International Airport/Brightline highspeed passenger train and just over an hour to dip your toes in salty water and sand on Florida's World Famous Beach in Daytona. Downstair units with perfect location do not come around often so book your private tour today and ask your REALTOR for the video walk through link.
Listing is courtesy of: BONJORN REAL ESTATE (352-394-2112)
Listing Agent: Mendy Bacon (407-383-7213)
515 9TH ST, WINTER GARDEN, FL 34787
$279,90082 Days on yellowkey MLS ID: O6383185
5 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 770 Built: 1951 Tax: $1,285 (2024)Community: Merchants SubSingle Family
Taxes:$1,285
Remarks: Under contract-accepting backup offers. Welcome to 515 9th St in Winter Garden, a fully renovated, move-in ready home just minutes from vibrant downtown shopping, dining, and the West Orange Trail. This beautifully updated property features a bright, functional layout with modern finishes and comfortable living spaces perfect for everyday living and entertaining. Natural light fills the home, creating a warm and inviting atmosphere throughout. The spacious yard offers plenty of room to relax, garden, or design your ideal outdoor retreat. Enjoy the convenience of nearby parks, schools, and major roadways while living in one of Central Florida’s most sought-after communities. Don’t miss your chance to own this turnkey Winter Garden gem.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Shane Jordan (407-866-3575)
5618 WATER ROSE RD, WINTER GARDEN, FL 34787
$395,00020 Days on yellowkey MLS ID: O6400788
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1755 Built: 2016Monthly Fee: $402 Tax: $6,527 (2025)Community: Signature Lakes Ph 3B-6Townhouse
Taxes:$6,527
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: This two-story townhome consists of three bedrooms, two and a half bathrooms, and a two-car rear load garage. The kitchen, family room, combination living room and dining room, and a laundry room with washer and dryer are located on the first floor. The upstairs master suite has a private bathroom and a walk-in closet. Independence Townhomes offers residents maintenance-free living without sacrificing amenities. Amenity highlights include an on-site boat launch, swimming pool, fitness center, sports courts, and more! Must see!!
Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)
Listing Agent: Isabel Sirizzotti (407-361-8236)
12529 DALLINGTON TER, WINTER GARDEN, FL 34787
$884,99020 Days on yellowkey MLS ID: O6400678
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3519 Built: 2006Monthly Fee: $130 Tax: $6,735 (2025)Community: Foxcrest A-N & PSpa: YesSingle Family
Taxes:$6,735
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Welcome to 12529 Dallington Terrace, a beautifully upgraded 5 bedroom, 3.5 bathroom POOL HOME offering over 3,500 square feet of thoughtfully designed living space and the perfect blend of comfort, functionality, and RESORT-STYLE OUTDOOR LIVING in one of Winter Garden’s most desirable locations. From the moment you arrive, the home makes a strong impression with its manicured landscaping and inviting covered entry. Inside, you’re greeted by a bright, open layout featuring an elegant COFFERED TRAY CEILING, neutral finishes, and a well-designed floor plan that includes a PRIVATE OFFICE, FORMAL LIVING ROOM, and FORMAL DINING ROOM—offering both flexibility and defined spaces for entertaining. The heart of the home is the open-concept kitchen, complete with GRANITE COUNTERTOPS, abundant cabinetry, bar seating, and a dedicated DINETTE area, all flowing seamlessly into the main living space. Large sliding glass doors create a true indoor-outdoor connection, filling the home with natural light and opening to the backyard retreat. PLANTATION SHUTTERS throughout add a timeless, upscale touch, while a WHOLE-HOME AND PATIO SPEAKER SYSTEM enhances both everyday living and entertaining. The primary suite offers a spacious and private retreat, while the additional bedrooms are well-sized and thoughtfully positioned for family or guests. Upstairs, a generous LOFT / BONUS ROOM serves as a dedicated ENTERTAINMENT SPACE and is currently set up as a PRIVATE THEATER ROOM—perfect for movie nights, sports, or gaming. Step outside to what truly sets this home apart—a MASSIVE 57’ x 43’ SCREENED-IN OUTDOOR LIVING AREA designed to feel like your own private resort. The custom pool features a HEATED SPA / JACUZZI, built-in SWIM-UP BAR SEATING, decorative FOUNTAIN WATER FEATURES, and a FULL OUTDOOR KITCHEN AND GRILL AREA WITH GAZEBO, creating the ultimate space for hosting and relaxing. FLORIDA GLASS SCREENING along portions of the enclosure provides added PRIVACY while maintaining natural light. Major updates include a NEWER ROOF (July 2022) and HVAC (2020), offering peace of mind for the next owner. Ideally located just minutes from WINTER GARDEN VILLAGE, DOWNTOWN WINTER GARDEN, and PLANT STREET, with easy access to TOP-RATED RESTAURANTS, COFFEE SHOPS, breweries, retail, community events, farmers markets, major highways, and close proximity to DISNEY and A-RATED SCHOOLS, this home offers both convenience and an exceptional lifestyle. The Foxcrest community offers great lifestyle amenities as well, such as the community pool, park/playground, tennis courts, and clubhouse! This property delivers a rare combination of SPACIOUS INTERIOR DESIGN, MULTIPLE ENTERTAINMENT AREAS, and a TRUE BACKYARD SHOWPIECE—an exceptional opportunity in this community.
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Andrew Kincaid (407-304-0454)
14501 GROVE RESORT AVE, WINTER GARDEN, FL 34787
$349,90020 Days on yellowkey MLS ID: S5148274
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 2009Monthly Fee: $608 Tax: $6,218 (2025)Community: Grove Resort And SpaCondo
Taxes:$6,218
Remarks: Turnkey 2-bedroom fully furnished and equipped condo-hotel residence at The Grove Resort & Water Park Orlando, just minutes from Walt Disney World and Orlando’s top attractions. Unit 3632 offers the perfect combination of personal enjoyment and income-producing potential in one of Central Florida’s most desirable vacation destinations. This spacious residence features an open-concept layout, modern kitchen with granite countertops and stainless steel appliances, comfortable living and dining areas, and a private balcony ideal for relaxing after a day in the parks. The highly desirable two-bedroom floor plan appeals to families and groups, creating strong rental demand and excellent short-term rental potential. Whether you are seeking a second home, vacation retreat, or investment property, this is a true turnkey opportunity ready for immediate use or rental. Owners and guests enjoy world-class resort amenities including a private water park, lazy river, multiple pools, surf simulator, full-service spa, fitness center, on-site restaurants and bars, arcade, family activities, shuttle service to the theme parks, and professional on-site management. Located in the heart of Orlando’s thriving tourism market with year-round visitors, this property offers exceptional lifestyle value and strong investment appeal. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Migdalia Croes (888-883-8509)
13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$867,00028 Days on yellowkey MLS ID: O6398468
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2186 Built: 1994Monthly Fee: $69 Tax: $6,434 (2025)Community: Sunset LakesSpa: NoSingle Family
Taxes:$6,434
Remarks: Beautifully updated single-story home featuring 4 bedrooms and 3 bathrooms, situated on an expansive lot of over half an acre in the desirable Sunset Lakes community. This residence offers a spacious layout ideal for comfortable living and has been fully remodeled throughout. The home features a great gourmet kitchen with a large island and sleek Dekton countertops, perfect for both everyday living and entertaining. Step outside to a stunning backyard retreat with a private pool and screened enclosure, ideal for year-round enjoyment. Ideally located just minutes from Highway 429, Winter Garden Village, and world-renowned attractions like Walt Disney World, this property also benefits from access to highly rated A-grade schools, making it an exceptional opportunity in one of Winter Garden’s most sought-after areas.
Listing is courtesy of: VALSTAR REALTY LLC (407-270-5000)
Listing Agent: Otto Solis Parraga (407-431-1789)
2131 TALL OAK DR, WINTER GARDEN, FL 34787
$890,00073 Days on yellowkey MLS ID: O6385247
2 Days Off yellowkey (back on 4/20/2026)
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3282 Built: 2000Monthly Fee: $92 Tax: $8,475 (2024)Community: Wintermere PointeSingle Family
Taxes:$8,475
Elementary School: Whispering Oak Elem
Remarks: Welcome to Wintermere Pointe, one of Winter Garden’s most established gated communities, and to a residence defined by scale, light, and thoughtful renovation. The home’s symmetrical facade and covered entry create a strong architectural presence, leading into a dramatic double-height foyer framed by expansive arched windows. Natural light reflects across Italian porcelain flooring, while a striking split-face stone accent wall extends vertically alongside the staircase, adding texture and depth to the open space. The fully renovated kitchen is both refined and functional, featuring waterfall quartz countertops, custom solid-wood cabinetry, marble designer backsplash, integrated wine storage, stainless steel appliances, under-cabinet lighting, and a contrasting island that anchors the room. The open layout connects seamlessly to the family room, where oversized windows overlook the fenced backyard and fill the space with natural light. Upstairs, luxury vinyl plank flooring replaces carpet entirely, creating continuity and durability throughout. According to public records, the home offers 5 bedrooms and 3 bathrooms, plus an additional bathroom added by the current owner. The primary suite combines comfort and modern elegance, offering tray ceilings, direct access to the backyard, and a spa-inspired bathroom finished with large-format marble-look tile, a walk-in shower, and a dedicated vanity area. A dedicated cinema room delivers a true theater experience, the perfect setting for movie nights and gatherings. It’s an exceptional feature for entertaining or quiet evenings at home. Situated on a .28-acre fenced lot with mature landscaping, the property includes a 3-car garage and an extended driveway accommodating up to six vehicles. Major improvements include the roof (2018), A/C unit (2025), and septic system (2020). Located minutes from SR-429 and Winter Garden Village, the home offers convenient access to shopping, dining, and everyday amenities while preserving the privacy of gated living.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Ane Rodrigues (407-488-3480)
14345 WABASSO LOOP, WINTER GARDEN, FL 34787
$735,00094 Days on yellowkey MLS ID: O6376609
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 2022Monthly Fee: $192 Tax: $10,615 (2025)Community: Tilden Place/Winter GardenSingle Family
Taxes:$10,615
Remarks: Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Garden’s most convenient locations. The main level features a private primary suite along with three additional bedrooms, including an en suite option ideal for guests, multigenerational living, or a home office. Upstairs, a spacious loft, bedroom, and full bath create a separate retreat perfect for teens, visitors, or work-from-home needs. Light-filled living and dining areas flow into the kitchen, which is well-appointed with a gas range, double ovens, generous counter space, a walk-in pantry, and breakfast bar—designed to support both everyday living and effortless entertaining. Sliding doors open to a screened porch, extending the living space outdoors for relaxed mornings and evenings. Enjoy close proximity to A-rated schools, including Keene’s Crossing, Bridgewater Middle, Windermere High, and nearby Foundation Academy. Just minutes from downtown Winter Garden, the West Orange Trail, shopping, dining, and daily conveniences, with easy access to SR 429, Orlando International Airport, and the attractions Central Florida is known for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
15182 SUNRISE GROVE CT, WINTER GARDEN, FL 34787
$394,90065 Days on yellowkey MLS ID: O6382211
REDUCED by $4,100 (1.0%) on 04/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1844 Built: 2018Monthly Fee: $346 Tax: $3,222 (2024)Community: Hickory Hammock Ph 2BTownhouse
Taxes:$3,222
Middle School: Hamlin Middle
Remarks: Welcome to 15183 Sunrise Grove Court, a beautiful townhome located in the highly sought-after Hickory Hammock community in Winter Garden, Florida, where comfort, lifestyle, and an excellent location come together perfectly. Offering 1,844 square feet of living space and 2,393 total square feet, this property features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing the layout and space today’s families truly value. From the moment you enter, you are welcomed by a bright, open design filled with natural light that creates a sense of spaciousness and warmth. The seamless connection between the living room, dining area, and kitchen creates the perfect environment for family gatherings, entertaining guests, or simply enjoying everyday life in comfort. The kitchen becomes the heart of the home, strategically connected to the main living areas so you can always stay part of every moment. Whether hosting special gatherings or enjoying quiet evenings at home, this space easily adapts to your lifestyle. On the second level, the primary suite offers a private retreat ideal for rest and relaxation. Spacious and thoughtfully designed, it provides both comfort and privacy. The additional bedrooms are versatile and can easily be used as family bedrooms, guest rooms, or a home office. Hickory Hammock is more than just a community—it’s a lifestyle. Residents enjoy resort-style amenities including a clubhouse, pool, fitness center, playground, and scenic walking trails surrounded by beautifully maintained green spaces. It’s a place where neighbors connect, families spend time together, and the atmosphere is peaceful and welcoming. Strategically located in Winter Garden near Horizon West, the property offers convenient access to highly rated schools, shopping centers, restaurants, major roadways, and the charm of Historic Downtown Winter Garden. It is also just a short drive from Orlando’s major employment centers and the area’s most popular attractions. Homes in this community are highly sought after and do not stay on the market for long. If you are looking for a home that combines space, comfort, and a true sense of belonging, 15183 Sunrise Grove Court may be exactly what you have been waiting for. Schedule your private showing today and come experience it in person.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Natsue Siqueira (407-722-0850)
9459 JAYWOOD RD, WINTER GARDEN, FL 34787
$755,00069 Days on yellowkey MLS ID: O6386488
REDUCED by $5,000 (0.7%) on 04/20/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2840 Built: 2020Monthly Fee: $261 Tax: $6,669 (2025)Community: Waterleigh Ph 3ASingle Family
Taxes:$6,669
Remarks: BACK ON MARKET DUE TO BUYER FINANCING FALLING THROUGH!! AS-IS sale with peace of mind! All prior repair requests have been completed, and a previous buyer’s inspection report is available for review. Back on market due to buyer financing, no fault of seller. Take advantage of a $5,000 exterior painting credit & ask about this incentive! Welcome to this stunning 5-bedroom, 4-bathroom home in the highly sought-after Waterleigh community in the heart of Horizon West, Winter Garden. This property is the perfect blend of luxury, comfort, and convenience and offers the PERFECT multi-generational home layout. Zoned for Atwater Bay Elementary School, this home is ideally positioned within a thriving and growing community. As you step through the front door, you’ll be immediately impressed by the spacious, open floor plan. To the right, you’ll find a private 5th bedroom, complete with a full walk-in shower just outside, ideal for guests or a quiet retreat. Continuing through the home, you'll be greeted by a seamless flow between the expansive living and dining areas. The kitchen is designed for both function and style and now features custom shelving in the pantry, providing enhanced organization and storage. Beneath the staircase, there’s a generous storage closet, and the entire home boasts brand-new carpet less than two years old, offering both comfort and style. The property is also equipped with rain gutters for added protection. Upstairs, you'll discover the luxurious primary suite, along with three additional bedrooms. The oversized loft area includes a converted den, perfect for use as an office, media space, or flex room to fit your lifestyle. The primary bathroom is a true retreat, featuring both a shower and separate soaking tub, along with a massive walk-in closet. For ultimate convenience, the laundry room is located upstairs and includes a smart leak detection system. The washer and dryer are less than three years old and practically brand new. Step outside to your screened-in lanai, ideal for outdoor entertaining, relaxing evenings, or enjoying nightly fireworks from Walt Disney World along with AMAZING views of NASA rocket launches from the Space Coast. Located just minutes from Disney, this home also provides incredible convenience within the community itself, with Publix now open, Jersey Mike’s, McDonald's, a nail salon, and more nearby. Even more exciting, a bank is coming soon, adding to the ease of everyday living. The neighborhood is golf cart-friendly and filled with abundant amenities and community events, making it easy to stay connected and entertained year-round. Don’t miss the opportunity to make this dream home YOURS! Schedule your private showing today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
15350 OAK APPLE CT #17B, WINTER GARDEN, FL 34787
$329,90030 Days on yellowkey MLS ID: O6396724
0 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008Monthly Fee: $282 Tax: $2,474 (2025)Community: Tucker OaksCondo
Taxes:$2,474
Remarks: Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 baths and 2 car garage is taken care of with Pride and Joy. Home is in Immaculate condition. Home flows from room to room with the primary en suite on the second floor. Also has lots of built in storage and overhead storage in the garage. Offers a screened in porch with no rear neighbors for relaxing and family time. Conveniently located near shopping, dining, major highways and historic downtown Winter Garden, Oakland & The West Orange Trail.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Tracy Hampstead (407-803-3137)
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