Location: Winter Garden
Do Not Show Listings
1005 CHASE DR, WINTER GARDEN, FL 34787
$629,000156 Days on yellowkey MLS ID: A4674195
REDUCED by $10,000 (1.6%) on 05/07/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2319 Built: 2005Monthly Fee: $68 Tax: $7,086 (2024)Community: Island Pointe SubSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,086
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: LUXURY RENOVATED 4-BED HOME WITH NEW ROOF + AC — OVERSIZED 3-CAR GARAGE — MOVE-IN READY This beautifully renovated 4-bed, 2.5-bath single-family home in the heart of Winter Garden (34787) is truly move-in ready — offering a luxury 2025 redesign from top to bottom. Located in the highly desirable Golf Cart District, this home sits on a quiet cul-de-sac just minutes from Downtown Winter Garden, Plant Street Market, and the West Orange Trail. The interior features a bright open floor plan with dramatic double-height ceilings, brand-new tile flooring downstairs and durable LVP upstairs, all-new baseboards and trim, and a fully updated 2025 kitchen with stone countertops and modern cabinetry. The spa-style primary suite includes two walk-in closets, a glass walk-in shower, and a soaking tub. Major upgrades include a new roof, new AC, updated electrical and plumbing, and fresh exterior paint — making this home feel like new construction. The oversized 3-car garage provides rare extra storage and golf cart space. Only 4 minutes to Newton Park with a public boat ramp — perfect for lake access, sunsets, and outdoor recreation. Schedule your private showing today!
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
921 BENDING OAK TRL, WINTER GARDEN, FL 34787
$575,0002 Days on yellowkey MLS ID: O6405328
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2481 Built: 2012Monthly Fee: $125 Tax: $3,791 (2025)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$3,791
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: One or more photo(s) has been virtually staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
13332 SUBURBAN TER, WINTER GARDEN, FL 34787
$714,9009 Days on yellowkey MLS ID: O6402778
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2706 Built: 1994 Tax: $2,841 (2024)Community: Citrus Cove Unit 01Single Family
Taxes:$2,841
Remarks: Welcome to a rare opportunity in sought-after Winter Garden! This spacious multi-level residence offers 4 bedrooms, 3 bathrooms, a private in-law suite with separate entrance and kitchenette, and an entertainer’s dream backyard with pool, cabana, outdoor kitchen, and oversized driveway. Situated on a generous .35-acre lot with no HOA, this home offers flexibility for multigenerational living, rental potential, boat parking, or work-from-home lifestyle. Impact windows and doors add long-term value and peace of mind. Conveniently located near shopping, dining, major highways, and lake access. A unique Florida lifestyle property you won’t find often.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$474,97554 Days on yellowkey MLS ID: S5145650
REDUCED by $25,020 (5.0%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1999Monthly Fee: $45 Tax: $1,458 (2024)Community: Traditions SubSingle Family
Taxes:$1,458
Elementary School: Dillard Street Elem
Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
16461 OLIVE HILL DR, WINTER GARDEN, FL 34787
$588,90097 Days on yellowkey MLS ID: O6379181
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2008 Built: 2019Monthly Fee: $127 Tax: $7,241 (2024)Community: HawksmoorSingle Family
Taxes:$7,241
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Beautiful modern single-family home featuring 3 bedrooms and 2.5 bathrooms, thoughtfully designed for comfort and style. The open-concept kitchen showcases quartz countertops, a breakfast island, luxury backsplash, and tall gray cabinets, creating a sleek and functional space.The first floor offers elegant tile plank flooring, a versatile flex space ideal for a home office or study, a convenient half bath, and extra storage with a closet under the stairs.Enjoy outdoor living in the extended screened patio, perfect for BBQs and gatherings, plus additional green space with the option to add a fence for extra privacy. Spacious bedrooms throughout, with a bright and inviting primary suite.Amazing Winter Garden location on Avalon Rd, just minutes from Hamlin, Flamingo Crossings, theme parks, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated schools.The community features clubhouse, resort-style pool, fitness center, splash area, trails, playground, dog park, and soccer field perfect for the whole family.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Lizandra Troisi Passos (321-337-9448)
16848 HAMLIN VISTA ALY, WINTER GARDEN, FL 34787
$540,00066 Days on yellowkey MLS ID: O6387459
REDUCED by $10,000 (1.8%) on 04/24/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 2024Monthly Fee: $200 Tax: $8,210 (2025)Community: Hamlin PointeSingle Family
Taxes:$8,210
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Discover the timeless appeal of the Newbury floor plan in the exclusive Hamlin Pointe community! This 2024-built two-story home offers 4 bedrooms, 3 full bathrooms, and 2,088 sq ft of thoughtfully designed living space. A versatile first-floor bedroom serves perfectly as a guest suite, home office, or multi-generational retreat. The open-concept great room and dining area are anchored by a gourmet kitchen featuring quartz countertops, upgraded cabinetry, stylish backsplash, and a built-in cooktop, oven, and microwave — ideal for both casual family meals and effortless entertaining. Upstairs, three additional bedrooms surround a spacious owner’s suite with a generous walk-in closet, plus a conveniently located laundry room. Outside, enjoy a covered patio for relaxing or dining al fresco, and the privacy of a detached two-car garage on a low-maintenance lot. Nestled in the heart of Hamlin within Horizon West — one of Orlando’s fastest-growing areas — Hamlin Pointe delivers walkable resort-style living at its best. Stroll or bike to the vibrant Hamlin Town Center along scenic Lake Hancock for dining, shopping, entertainment, and year-round events. Families love the top-rated schools, abundant parks, trails, and new medical facilities. Just minutes to Walt Disney World, downtown Winter Garden, Winter Garden Village, SR 429, and Florida’s Turnpike, this boutique community of only 53 homes offers the perfect blend of modern convenience, low-maintenance luxury, and long-term investment value in a location where others vacation every day.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Tyler Somers (561-713-8728)
615 LAKE COVE POINTE CIR, WINTER GARDEN, FL 34787
$849,95013 Days on yellowkey MLS ID: O6402551
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2465 Built: 2014Monthly Fee: $94 Tax: $8,422 (2025)Community: Lake Cove Pointe Ph 2Spa: YesSingle Family
Taxes:$8,422
Remarks: One or more photo(s) has been virtually staged. Welcome to the Downtown Winter Garden Golf Cart District where lifestyle and location just make sense. This 4 bedroom, 2 bath pool home blends thoughtful upgrades with a layout that actually works for real life. From the moment you walk in, the natural light and open flow stand out. The main living spaces connect seamlessly, creating an easy, inviting feel whether you are hosting or just enjoying a night in. Throughout the home you will notice custom woodworking details that add warmth and character. From built ins to trim work, these touches elevate the space and give it a more intentional, finished look you do not see in every home. The kitchen offers a clean, updated feel with modern finishes, refreshed cabinetry, and functional space that opens directly into the dining and living areas. It is designed to be both practical and a place people naturally gather. One of the biggest advantages of this home is the fully paid off whole home solar system paired with multiple battery backups. This means lower monthly costs and added reliability during storms or outages, something that continues to matter more and more. Step outside and you get your own private backyard setup. The pool and spa create a true stay at home retreat. Whether it is weekends with friends or a quiet evening, the space is set up to be enjoyed year round. The three car garage is a rare find in this area and gives you all the room you need for a golf cart, bikes, storage or hobbies. Living here is where this home really stands out. Hop on your golf cart and head straight into downtown Winter Garden, one of the most loved small town districts in Central Florida. If exercise is your thing you're just a short distance to pickleball and tennis courts, baseball fields and the outstanding West Orange Bike Trail!! You are minutes away from a nationally recognized farmers market, the Crooked Can Brewery, the splash pad, Plant Street Market and a full calendar of events throughout the year. From live music and seasonal festivals to outdoor dining and boutique shopping, there is always something happening. The entire area has that walkable, charming feel that makes it feel like a Hallmark town brought to life. You are also close to Horizon West, major highways, top rated schools, downtown Orlando and the theme parks, giving you the perfect mix of convenience and small town charm. Homes like this in this location do not come up often. If you are looking for a home with character, smart upgrades, and a lifestyle that people move here for, this is it.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787
$1,325,00018 Days on yellowkey MLS ID: O6401205
1 Days Off yellowkey (back on 5/10/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3904 Built: 2016Monthly Fee: $235 Tax: $8,218 (2025)Community: Hickory HammockSpa: YesSingle Family
Taxes:$8,218
Elementary School: Whispering Oak Elem
Remarks: Under contract-accepting backup offers. Tucked away on a Private Street within a quiet cul-de-sac in the highly sought-after Gated community of Hickory Hammock, this exceptional 5 Bedroom, 4 Bathroom residence offers 3,908 sqft of thoughtfully designed living space with captivating views of Lake Burnett. Perfectly positioned to capture both Lake and Conservation Vistas, this home delivers the rare combination of Privacy, Comfort, and an Elevated Lifestyle in one of Winter Garden’s Most Desirable Neighborhoods. From the moment you enter, soaring 20-foot Ceilings in the foyer create a grand sense of arrival, complemented by a Formal Dining Room and immediate Sightlines to the Sparkling Pool and Tranquil Lake beyond, an unforgettable first impression that sets the tone for the entire home. Designed for both everyday living and entertaining, the first floor features Wood Plank tile throughout and an open, functional layout. The kitchen serves as the heart of the home, appointed with New Quartz Countertops, Stainless Steel Appliances, a Double Oven, abundant cabinetry, and an expansive Walk-in Pantry just off the Butler’s Pantry, complete with a JennAir Beverage and Wine Fridge. Thoughtful Lighting throughout enhances the warmth and livability of each space. Step outside to your Private Outdoor Retreat, where a Covered and Screened Lanai frames Peaceful Lake and Conservation Views. The Saltwater Pool with a Baja Shelf and Heated (electric) Spa invites year-round enjoyment, while the Spacious Backyard offers Plenty of Room for Kids or Pets to play, all while enjoying Stunning SUNSET VIEWS each evening over Lake Burnett and the Johns Lake Conservation area. A First-Floor Bedroom with a Full Bath provides flexibility for guests or multi-generational living. Upstairs, a generous Bonus Room offers endless possibilities for a media room, playroom, or additional living space. The Primary Suite is a true retreat, featuring Double Tray Ceilings and a Private Screened Balcony overlooking Lake Burnett, offering the perfect setting to take in breathtaking Sunset Views each evening. Secondary Bedrooms are well-appointed with Walk-in Closets, including one bedroom with an Ensuite Bathroom, while the remaining 2 Bedrooms share a well-designed bath. The tandem 3-Car Garage provides ample space for vehicles and storage, complemented by a spacious first-floor Laundry Room featuring New Quartz Countertops, a Sink, ample Cabinetry, and a Walk-in Closet. Residents of Hickory Hammock enjoy an impressive array of amenities including a Clubhouse, Fitness Center, Resort-style Pool, Fishing Pier, Tennis Courts, Sand Volleyball Courts, Dog Park, Playground, Walking Trails, and Golf-Cart-friendly streets. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, Top-Rated Schools, and approximately 20 miles to Orlando International Airport. This home offers the Perfect Blend of Space, Functionality, and Desirable Water View Living - schedule your private showing TODAY.
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Denise Gregorie (407-463-0080)
1032 BURLAND CIR, WINTER GARDEN, FL 34787
$529,99012 Days on yellowkey MLS ID: O6401764
INCREASED by $10,000 (1.9%) on 05/10/2026
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2487 Built: 2005Monthly Fee: $64 Tax: $6,728 (2025)Community: Fullers Xing Ph 03 A-GSingle Family
Taxes:$6,728
Remarks: Under contract-accepting backup offers. Spacious and inviting, this 5-bedroom, 2-bathroom home with one of the largest lots, boasting just shy of .4-acre in the Fullers Crossing community offers the perfect blend of comfort, style, and functionality. Thoughtfully updated, this home features a new roof (2020), water heater, and gutters (2021), along with a new A/C system (2023), giving you peace of mind for years to come. As you arrive, the paver driveway and two-car garage immediately enhance the home’s curb appeal. Step inside to find (newer) stylish luxury vinyl flooring that flows throughout the entire home, creating a cohesive and modern look. Designed with flexibility in mind, the layout includes a formal living room for gatherings and a formal dining room perfect for hosting memorable meals. At the heart of the home, the kitchen opens seamlessly to the family room and breakfast nook, creating a bright and airy living space enhanced by vaulted ceilings. The kitchen is equipped with stainless steel appliances, a brand-new range and microwave, a breakfast bar, and a pantry. The dinette area is ideal for casual dining and flows effortlessly into the family room. Abundant natural light from the sliding glass doors, combined with soaring ceilings, creates an open and inviting atmosphere. The spacious primary suite serves as a private retreat, complete with a walk-in closet and an ensuite bathroom featuring dual sinks, a separate shower, and a relaxing garden tub—perfect for unwinding at the end of the day. Four additional generously sized bedrooms provide plenty of space for family, guests, or a home office, along with a versatile flex space or bonus room to suit your needs. Situated on an oversized 0.39-acre lot, the outdoor space offers endless possibilities. Step outside to enjoy a covered patio overlooking a large, fully fenced backyard with durable vinyl fencing and a community wall for added privacy. Additional outdoor features include a shed (2018) and a double gate entry for convenient access. Only minutes to the beautiful downtown Winter Garden! Access to the West Orange bike trail is just outside the community. This home truly offers space, comfort, and versatility for any lifestyle. Don’t miss your opportunity to own this beautifully maintained and well-designed property—schedule your private showing today.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Scott Bedsole (407-914-8223)
15051 GROVESIDE RD, WINTER GARDEN, FL 34787
$483,5752 Days on yellowkey MLS ID: O6406358
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 2026Monthly Fee: $247 Tax: $1,375 (2025)Community: Parkview At HamlinTownhouse
Taxes:$1,375
Remarks: Under Construction. Ready estimate in August! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your Study Room with Storage space. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
6153 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$680,0301 Day on yellowkey MLS ID: G5112171
0 Days Off yellowkey (back on 5/9/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community, in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria, an award-winning single-story, open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, ample counter space, and an open layout that connects directly to the living areas, making it perfect for everyday living and entertaining. The owner’s suite and additional bedrooms are thoughtfully placed to maximize privacy and comfort. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
16664 CORDOBA, WINTER GARDEN, FL 34787
$139,0001 Day on yellowkey MLS ID: O6406490
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1993Community: Vista Del LagoManufactured Home
Remarks: GREAT OPPORTUNITY IN VISTA DEL LAGO! Move-in ready, Turn Key Ready! Furnished and just minutes away from Disney, right next to Margaritaville! Quiet Surroundings and peaceful community. This beautiful 3-bedroom, 2-bathroom mobile home comes fully furnished and offers everything you need to enjoy the Florida lifestyle. Golf cart garage, New roof, New water heater, Gated community,3 community pools, 2 pools heated and with Spa, Basketball courts, Pickleball courts,Amazing amenities. Ready to move in! Whether you’re looking for a primary residence, vacation getaway, or investment opportunity, this home is a must-see! Vista Del Lago Prime location near shopping, dining, attractions, and entertainment.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Annie Resto (407-900-6119)
13552 AUTUMN HARVEST AVE, WINTER GARDEN, FL 34787
$530,000Listed 05/09/2026 11:04PM MLS ID: O6404264
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1955 Built: 2025Monthly Fee: $343 Tax: $2,022 (2025)Community: Harvest/OvationTownhouse
Taxes:$2,022
Remarks: Beautifully maintained home located in the highly desirable area of Winter Garden! This spacious property offers the perfect blend of comfort, style, and convenience, featuring an open-concept floor plan, generously sized bedrooms, and abundant natural light throughout. The modern kitchen is ideal for entertaining, complete with ample cabinet space and a functional layout that flows seamlessly into the living and dining areas. Enjoy relaxing evenings in the private backyard with space for outdoor gatherings and family fun. Conveniently located near top-rated schools, shopping, dining, major highways, and world-famous attractions. A wonderful opportunity to own a beautiful home in one of Central Florida’s most sought-after communities—schedule your private showing today!
Listing is courtesy of: REALTY ONE GROUP EVOLUTION (786-477-4715)
Listing Agent: Milena Nunez (407-247-1814)
13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$1,150,00024 Days on yellowkey MLS ID: O6399227
REDUCED by $50,000 (4.2%) on 05/04/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3389 Built: 1998Monthly Fee: $69 Tax: $10,940 (2025)Community: Sunset LakesSpa: YesSingle Family
Taxes:$10,940
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Diane Sterling (407-761-0512)
833 BENDING OAK TRL, WINTER GARDEN, FL 34787
$435,0002 Days on yellowkey MLS ID: O6403683
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1789 Built: 2009Monthly Fee: $447 Tax: $4,032 (2025)Community: Oaks/Brandy Lake OTownhouse
Taxes:$4,032
Remarks: Beautifully maintained and truly turn-key, this 3-bedroom, 2.5-bath townhome is the kind of home where you can simply move in and start enjoying everything Winter Garden has to offer from day one, all while being located in the highly sought-after Golf Cart District just moments from the heart of charming Downtown Winter Garden! From the moment you walk in, you’re welcomed by bright, open living spaces, thoughtful design, and timeless finishes that make the home feel warm, elevated, and instantly inviting. Plantation shutters throughout add that polished custom touch, while the open-concept layout creates the perfect flow for both everyday living and entertaining. Upstairs, the spacious primary suite feels like its own private retreat, thoughtfully positioned away from the guest rooms so you can truly enjoy your own space. Wake up to beautiful open skies and unwind each evening with stunning sunset views right from your bedroom. This is townhome living exactly how it should be. Where else in Winter Garden can you enjoy a home like this, have pool access just a short walk away, and spend your weekends enjoying life instead of worrying about exterior upkeep? Lock it, leave it, travel when you want, and come home to a space that always feels effortlessly cared for. And the location? It’s hard to beat! Bending Oak Trail offers that true neighborhood feel with peaceful evening walks, friendly neighbors, and a sense of community that makes you feel right at home, all while being just moments from the heart of Downtown Winter Garden—one of Central Florida’s most beloved downtowns, known for its brick-lined streets, incredible local restaurants, charming boutiques, cozy coffee shops, weekend Farmer’s Market, and year-round community events that make this area so special. Hop on your golf cart and head down Plant Street for your morning coffee, dinner with friends, shopping, or an evening stroll. Even better, you’re right next to the West Orange Trail, making morning bike rides, walks, and outdoor living part of your everyday lifestyle. With quick access to 429, the Turnpike, SR-50, Disney, Downtown Orlando, and Orlando International Airport, convenience is seamlessly built into daily life. Winter Garden continues to be one of Central Florida’s most sought-after communities, and opportunities to own something this move-in ready, this well-located, and at this price point are incredibly hard to find.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
13603 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$787,00011 Days on yellowkey MLS ID: G5111474
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2425 Built: 1995Monthly Fee: $69 Tax: $5,322 (2025)Community: Sunset LakesSpa: YesSingle Family
Taxes:$5,322
Remarks: Under contract-accepting backup offers. Located in the heart of Winter Garden, this original-owner custom pool home offers both convenience and charm, just minutes from the 429, Winter Garden Village, area theme parks, hospitals, and everyday shopping. Situated on a large lot with mature trees, lush landscaping, and fruit trees, the home features 4 bedrooms and 2.5 bathrooms with a thoughtfully designed split floor plan. Inside, you’ll find tall ceilings, a formal living and dining room, and an open-concept kitchen and living area complete with a cozy fireplace and eat-in nook. The spacious primary suite includes an en-suite bathroom, while additional highlights include a screened-in pool enclosure, large driveway, climate-controlled storage area, and a laundry room with sink and ample storage. This home blends comfort, space, and location in one exceptional opportunity.
Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)
Listing Agent: Chelsea Eckert (407-455-2785)
199 E CREST AVE, WINTER GARDEN, FL 34787
$525,00017 Days on yellowkey MLS ID: O6401923
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1659 Built: 1984 Tax: $6,857 (2025)Community: Garden Heights SubSpa: NoSingle Family
Taxes:$6,857
Remarks: Welcome to 199 E Crest Ave, a recently updated residence featuring fresh interior paint and partial flooring replacement throughout. The kitchen includes all stainless steel appliances and an accent backsplash for a polished finish. This home also contains a cozy fireplace and a covered patio, providing space for relaxation. Experience modern updates and practical comfort in this prepared home. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,287,00041 Days on yellowkey MLS ID: O6394059
REDUCED by $30,000 (2.3%) on 05/09/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4019 Built: 2018Monthly Fee: $188 Tax: $17,895 (2025)Community: Canopy Oaks Ph 1Single Family
Taxes:$17,895
Remarks: A rare opportunity in a desired luxury neighborhood. A home designed for the way you live today, where walls of glass open completely, blending indoor and outdoor spaces into one seamless experience. In the gated community of Canopy Oaks, this A.R. Bailey Homes LLC Delray model offers elevated design, flexibility and everyday convenience. Well-maintained and only eight years young, this residence is set within an intimate enclave of just 49 homesites, offering a rare sense of privacy while remaining ideally positioned on Roper Road between Winter Garden’s historic downtown district and the Winter Garden Village shopping complex. From moment you arrive, the home makes a lasting impression with high-end driveway pavers, a durable concrete tile roof, woodgrain garage doors, stone facade accents and grand 8-foot solid wood arched double entry doors. Inside, the layout unfolds with intention, balancing elegant design and functional living. At the center of the home, the kitchen is designed to bring people together, featuring a natural gas cooktop with exterior venting, a built-in oven, upgraded appliances, a pot filler, 42-inch cabinetry with crown molding, a tile backsplash, under-cabinet lighting, a walk-in pantry and a large island that opens to the great room with coffered ceilings. Just beyond, a wine cellar with an iron gate adds a distinctive focal point for entertaining. The first-floor primary suite offers a peaceful retreat with a soaking tub, an oversized walk-in shower with dual heads and a bench, dual granite vanities and a custom closet system. A secondary first-floor, en-suite bedroom or office provides flexibility, while upstairs features a second primary suite, two additional en-suite bedrooms, a loft, a guest half bath and a covered rear balcony for added privacy and comfort. The standout is the home’s seamless indoor-outdoor connection. A full corner-opening glass wall, along with three-panel stackable sliding doors, extends the dining and great rooms to a covered lanai with a motorized retractable screen, creating a natural flow for entertaining or everyday living. The spacious backyard, framed by a concrete stucco privacy wall, offers a blank canvas for a future pool or custom outdoor retreat. Thoughtful upgrades continue throughout, including motorized custom light filtering roller shades in the dining and great rooms, dual tankless water heaters, two air-conditioning units with zoned climate control, mudroom, a reading nook and elegant iron stair railings. Residents of Canopy Oaks also enjoy a nature trail and a children’s play park. With proximity to downtown Winter Garden, Winter Garden Village, area hospitals, shopping, dining and major roadways including Florida Turnpike, state roads 429 and 408, and Interstate 4, this home presents a compelling opportunity to experience a lifestyle where design, comfort and location come together effortlessly.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Lisa Rutkowski (407-793-2416)
1968 PANTHEON DR, WINTER GARDEN, FL 34787
$529,9003 Days on yellowkey MLS ID: O6404386
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1971 Built: 2015Monthly Fee: $211 Tax: $3,832 (2025)Community: Alexander RdgSingle Family
Taxes:$3,832
Remarks: Beautifully maintained home in the Heart of Winter Garden! Located in the highly sought-after neighborhood of Alexander Ridge, this single story Craftsman-style home embodies the feeling of a peaceful family community, with its stone-covered columns and a welcoming front porch. Continuing through the wide foyer you'll find a den/flex room, well-suited for a home office or playroom. The upgraded kitchen with thick quartz countertops, 42” solid wood cabinets, and a large island, is open to the dining and family rooms, making it ideal for entertaining. At the end of the day, the expansive owners' suite is a true retreat, featuring a massive walk-in closet, dual vanities, a soaking tub, and a large upgraded walk-in shower. Set apart from the Owners' suite, you'll find the two additional bedrooms, a tasteful guest bath, and the spacious laundry room. Step outside to the relaxing covered and screened lanai, perfect for enjoying the evening breezes in privacy. Situated in a fantastic community with a neighborhood park, gazebo, miles of trails, and a refreshing pool, you'll be just minutes from the best of Hamlin and Winter Garden—shopping, dining, and top-rated schools. Although the serenity feels like its own little world, you're only a short drive to Disney World®, Universal Studios® and all the attractions Central Florida has to offer. Don’t miss this incredible opportunity—schedule your showing today!
Listing is courtesy of: KUNKLE REALTY GROUP (844-978-7750)
Listing Agent: Greer Kunkle (321-250-0106)
12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787
$750,00032 Days on yellowkey MLS ID: O6397592
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2858 Built: 2026Monthly Fee: $140Community: Harvest At OvationSingle Family
Remarks: Under Construction. What's Special: Flat Lot | Close to Amenity | Flex Room. New Construction - May Completion! Built by America's Most Trusted Home Builder. Welcome to the Ozark at 12983 Harvest Rain Avenue in Harvest at Ovation! This new home has an inviting gallery-style foyer welcoming you inside and leads past a dedicated study into the open main living area where the dining space flows seamlessly into the gathering room and gourmet kitchen. The kitchen shines with quartz countertops, an apron front stainless steel kitchen sink, cabinets at the kitchen island, and a spacious walk-in pantry designed to keep everything within reach. Pocket sliding doors from the gathering room open to an extended lanai, creating an easy connection between indoor and outdoor living. The primary suite is tucked quietly at the back of the home and features a spa-inspired en-suite bath and a large walk-in closet. Two secondary bedrooms, including one with its own en-suite bath, along with an additional full bath, powder room, nearby laundry area, and a two-car tandem garage complete this thoughtfully designed home. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Gourmet kitchen, study in place of flex, pocket slider at gathering room, shower at bath 3, extended lanai, 8' interior doors, second sink at bath 2, and whole house blinds. Photos are for representative purposes only. MLS#O6397592
Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)
Listing Agent: Michelle Campbell (407-756-5025)
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