Winding Bay Homes 

Winding Bay is a vibrant and sought-after community located in Winter Garden, Florida. It offers a diverse range of real estate options, including beautiful homes that cater to various lifestyles and preferences. The community boasts a range of amenities, such as a swimming pool, park, and playground, providing residents with a convenient and enjoyable living experience.

Aside from its excellent amenities, Winding Bay benefits from its close proximity to a plethora of nearby attractions. Just a short drive away, residents can explore the charming downtown area of Winter Garden, known for its historic architecture, boutique shops, and delicious dining options. Nature enthusiasts can also take advantage of the community's proximity to stunning lakes, parks, and golf courses, offering plenty of opportunities for outdoor recreation and relaxation.

Winding Bay's location provides easy access to major highways, allowing residents to venture out and enjoy the many attractions of Central Florida. From the world-famous theme parks of Walt Disney World and Universal Orlando Resort to the vibrant entertainment options of downtown Orlando, there is always something exciting to discover within a short drive from the community.

Available Winding Bay Homes For Sale

$722,000
3 Beds ⋅ 3 Baths ⋅ O6427810 MLS
Beautifully upgraded *POOL* home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home over 2,100 square feet of comfortable living space with modern finishes and an open floor plan filled with natural light. The spacious kitchen is truly the heart of the home, featuring a large quartz island, built-in oven and microwave, gas cooktop, stainless steel appliances, plenty of cabinet space, and a walk-in pantry.  Master Bedroom Suite offers a spa-like bathroom with dual vanities, a large walk-in shower, and a custom walk-in closet. The dedicated office with built-in cabinetry provides an ideal work-from-home space. The backyard offers your own private retreat with a heated saltwater pool, covered lanai, outdoor kitchen, pergola, and a fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. Additional features include: *Paid 100% Solar Panels*, luxury laminate flooring throughout the main living areas, a custom wood panel for the TV, a spacious laundry room with built-in cabinets and utility sink, an irrigation system, and a two-car garage with storage racks and an EV charger. Winding Bay enjoy resort-style amenities including a community pool, playground, dog park, and scenic walking paths, all conveniently located near Disney, Horizon West, shopping, dining, and top-rated schools.

15009 Lebeau Loop, Winter Garden

Courtesy of TOP HOUSING LLC

$644,000
5 Beds ⋅ 4 Baths ⋅ O6424514 MLS
A RARE FIND IN THE HIGHLY DESIRABLE WINDING BAY COMMUNITY! This beautifully designed home offers the perfect blend of comfort, flexibility, and income potential. One of its most impressive features is the FULLY EQUIPPED PRIVATE ONE-BEDROOM APARTMENT ABOVE THE GARAGE with its own private entrance, spacious living room, full kitchen, private bedroom, walk-in closet, laundry area, and full bathroom. The apartment is CURRENTLY TENANT-OCCUPIED, providing immediate rental income for the next owner while also offering incredible flexibility as a guest suite, multigenerational living space, or a completely private home office. The main residence features 4 spacious bedrooms and 2.5 bathrooms, with the PRIMARY SUITE CONVENIENTLY LOCATED ON THE FIRST FLOOR, offering comfort and privacy. The open-concept floor plan showcases elegant tile flooring throughout the main living areas, premium carpeting upstairs, 8-foot interior doors, upgraded lighting, and abundant natural light that creates a warm and inviting atmosphere. A standout architectural feature is the CHARMING SECOND-FLOOR FRONT PORCH, the perfect place to enjoy your morning coffee, unwind in the evenings, or simply relax while taking in the peaceful neighborhood views. Residents of Winding Bay enjoy resort-style amenities, including a community pool, splash pad, playground, and dog park, all with a low HOA fee. Ideally located just minutes from SR-429, approximately 10 minutes from Walt Disney World, and close to Horizon West Town Center, shopping, dining, and Orlando International Airport, this home is also zoned for highly rated schools. Whether you're looking for a primary residence with built-in rental income, a home designed for multigenerational living, or the convenience of a private apartment for guests or a dedicated workspace, this exceptional property truly offers the best of Central Florida living.

15068 Lebeau Loop, Winter Garden

Courtesy of FLORIDA CONNEXION PROPERTIES

$799,000
4 Beds ⋅ 4 Baths ⋅ O6422754 MLS
Beautifully decorated pool home in a prime Winter Garden location, zoned for highly rated A schools. This spacious 4-bedroom, 3.5-bath residence offers a private heated pool, 2-car garage, and an open-concept layout perfect for everyday living and entertaining. The first floor features a dedicated office, a flex/playroom that can also serve as a guest room, media room, or second office, plus a large kitchen that opens to the main living area and overlooks the outdoor pool space. Upstairs, enjoy a spacious loft, the primary suite, an additional ensuite bedroom, and two secondary bedrooms connected by a shared bathroom. The home is tastefully decorated, move-in ready, and conveniently located near shopping, dining, major roads, and everything Winter Garden has to provides. Furniture may be negotiated separately.

14931 Lebeau Loop, Winter Garden

Courtesy of WRA BUSINESS & REAL ESTATE

$549,900
4 Beds ⋅ 3 Baths ⋅ O6418437 MLS
Welcome to 15411 Gilligan Court, a beautifully maintained 2021 home in the sought-after Winding Bay community of Winter Garden! Offering 4 bedrooms, 2.5 bathrooms, and nearly 2,200 square feet of thoughtfully designed living space, this home packs an incredible amount of functionality and flexibility into its footprint. One of the most desirable features is the first-floor bedroom, making it a great option for guests, a private home office, gym, playroom, or flex space to suit your needs. Upstairs, you'll find the primary suite and remaining bedrooms conveniently located together, along with a versatile loft that can be used as a second living area, media room, homework station, or play space. The upgraded kitchen is the heart of the home, featuring modern finishes, ample cabinet space, and an open-concept layout perfect for everyday living and entertaining. Throughout the home you'll find tile and waterproof wood laminate flooring, with **no carpet anywhere**, creating a clean, cohesive look that is both stylish and easy to maintain. Step outside to enjoy the screened-in lanai and extended paver patio, creating additional outdoor living space perfect for relaxing, grilling, or entertaining friends and family. Located in one of Horizon West's fastest-growing areas, Winding Bay offers convenient access to Flamingo Crossings, Walt Disney World, major highways, shopping, dining, entertainment, and top-rated schools including Water Spring Elementary, Water Spring Middle, and Horizon High School. If you're looking for a newer home in an exceptional location that offers flexibility, low-maintenance living, and room for everyone, this one is a must-see!

15411 Gilligan Court, Winter Garden

Courtesy of EXP REALTY LLC

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