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$720,000
5 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
THE HEART OF WINTER GARDEN… Shopping and Dining just blocks away. Located in the Golf Cart District, the community of Winter Oaks is a hidden gem offering this beautiful 5-Bedroom, 3-Bath Traditional Home with 3000 sq/ft of living space. The rear alley garages allow for timeless architecture, majestic oaks and mature landscaping to set the stage for a lifetime of memories. The front porch leads to your 8’ entry door, open to volume ceilings, a 2nd floor balcony, outstanding crown molding and elegant wood floors. They say, you only have one chance at a first impression, but this home will keep making 1st impressions from front to back. The Living Room is 28x15, Kitchen, Breakfast area and Family room is 34x14 open to a magnificent screen room. The Primary bedroom on the 2nd floor is an impressive 22 x16 with a private balcony for your morning coffee or your evening glass of wine. The Neighborhood does include a community pool and a playground but you are a golf cart ride to the interactive Fountain and Splash pad, Downtown Lifestyle events like Friday’s on the Plaza, Saturday Farmer’s Market on the Pavilion, Holiday Events and Art Exhibits. This is one home you need to tour before you plant roots in Winter Garden.

627 Autumn Oaks Loop, Winter Garden
$715,000
5 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
STUNNING UPGRADED HOME IN THE HEART OF WINTER GARDEN Welcome to this beautifully upgraded 5-bedroom, 3-bathroom home located in one of Winter Garden’s most sought-after communities. From the moment you arrive, you’ll be captivated by the home’s curb appeal, water facing front porch, balcony views, and palm tree framed landscaping. Inside, you’ll find a thoughtfully designed layout with modern finishes throughout. The fully renovated kitchen features crisp white cabinetry, quartz countertops, navy lower cabinets with gold hardware, a large center island, and stainless steel appliances. Flowing seamlessly into the dining and living areas, the open-concept floor plan makes this home perfect for entertaining or everyday living. The spacious primary suite offers a peaceful retreat with vaulted ceilings, abundant natural light, and private balcony access overlooking serene water views. Additional bedrooms are generously sized, and the upgraded bathrooms showcase stylish finishes. Step outside to enjoy multiple outdoor living spaces, including a covered patio, fenced yard, and balcony—all perfect for relaxing or hosting gatherings. This community offers wonderful amenities, including a pool and playground just a short walk away. For added lifestyle perks, you’re only a golf cart ride from the lively Winter Garden Farmers Market and Historic Downtown Winter Garden, known for its shops, dining, and events. Plus, public pickleball courts are nearby for endless fun. This home blends modern upgrades, prime location, and community charm—making it the perfect place to call home!

724 Chase Oaks Court, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
This exceptional home is ideally located in the desirable Golf Cart District, offering park-side living with views of majestic oaks, expansive green space, and the iconic Winter Oaks water tower. Just steps from the community pool and playground, the property showcases upgrades rarely found at this price point. The versatile floor plan features a primary suite and two additional bedrooms on the main level, with wood flooring throughout the main living areas creating a seamless flow. The primary suite overlooks the park and includes a spacious walk-in closet with built-ins and a stylish sliding barn door leading to the renovated bathroom. The bath features quartz countertops, dual sinks, a modern freestanding tub, and a separate tile shower. A fourth bedroom or bonus room with its own full bath and walk-in closet occupies the upper level. This 19' x 15' space is ideal for guests or flexible use such as a media or game room. The open kitchen serves as the heart of the home, offering abundant cabinetry, quartz countertops, stainless steel appliances, and a center island with eight drawers designed for optimal functionality. Thoughtful updates are evident throughout the property. Outdoor living continues in the screened rear patio, designed for comfort and year-round enjoyment. The backyard features artificial turf and mature landscaping to enhance privacy and reduce maintenance. Located just a short golf cart ride from historic downtown Winter Garden, this home offers easy access to award-winning restaurants, boutique shopping, outdoor dining, the splash pad and fountain, weekly events, and seasonal celebrations. This is a beautifully maintained property that must be toured to fully appreciate its quality and design.

337 Sunset Oaks Rd, Winter Garden
$625,000
4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Winter Oaks, where move-in-ready comfort meets the highly sought-after Downtown Winter Garden golf cart lifestyle! This beautifully updated 4-bedroom, 3-bath home offers 2,308 square feet of thoughtfully designed living space with an open-concept floor plan, high ceilings, crown molding, and a versatile split-bedroom layout designed for both privacy and functionality. The current owners have continued to enhance the home with valuable upgrades, including LVP FLOORING THROUGHOUT, NEW APPLIANCES, a WHOLE-HOUSE GENERATOR, a newly added DECK, and UPDATED LANDSCAPING. Combined with a ROOF replaced in September 2022, these improvements offer the style, functionality, and peace of mind today's buyers are looking for. At the heart of the home, the spacious gourmet kitchen features 42-inch cabinetry, new stainless steel appliances, generous prep and storage space, and a large center island that opens to the main living area—perfect for entertaining and everyday gatherings. The primary suite is conveniently located on the first floor and offers a spacious walk-in closet and en-suite bathroom with dual vanities, a soaking tub, and separate walk-in shower. Two additional secondary bedrooms are also located on the main level, providing flexibility for family, guests, or a home office. Upstairs, you'll discover an exceptionally spacious 4th bedroom with its own private full bathroom, creating an ideal guest suite, multigenerational space, or private work-from-home setup. Outdoor living is another standout feature. Outside find the fully fenced backyard featuring a covered and screened lanai, paver patio, and newly added deck, creating multiple spaces for grilling, entertaining, pets, or simply relaxing in the Florida sunshine. Updated landscaping enhances the curb appeal and completes the home's welcoming outdoor setting. And then there's the location! Winter Oaks puts you just minutes from the heart of Historic Downtown Winter Garden, where you can bike, or take your golf cart to Plant Street and enjoy award-winning restaurants, breweries, boutique shopping, live entertainment, and the popular Winter Garden Farmers Market. Outdoor enthusiasts will appreciate convenient access to the West Orange Trail, while residents can also enjoy the neighborhood community pool and cabana. With convenient access to major roadways, Orlando attractions, shopping, dining, and everyday conveniences are all within easy reach.

880 Summer Oaks Road, Winter Garden
$580,000
3 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden!  Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom.   The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting.  Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC condenser and coils ) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home.  Schedule your private showing today!

638 Autumn Oaks Loop, Winter Garden