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

$775,000
3 Beds ⋅ 3 Baths ⋅ O6427810 MLS
Beautifully upgraded 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 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

$659,000
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

$749,000
3 Beds ⋅ 3 Baths ⋅ O6423067 MLS
Welcome to this beautifully upgraded 2020-built home in Horizon West offering 3 spacious bedrooms, 2.5 bathrooms, and a thoughtfully designed floor plan that blends style, comfort, and functionality. From the elegant formal living room to the expansive great room that seamlessly connects the kitchen, dining, and family areas, this home is perfect for both everyday living and entertaining.The heart of the home is the stunning chef's kitchen, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, and abundant workspace for cooking and gathering. Luxury tile flooring, upgraded in 2025, flows throughout the entire home, while crown molding, oversized baseboards, and decorative hallway columns add timeless architectural detail throughout the home.The spacious owner's suite offers a beautifully renovated spa-inspired bathroom, fully upgraded in 2026, creating a private retreat you'll love. A convenient Jack-and-Jill bathroom serves the secondary bedrooms, providing both functionality and privacy for family or guests.Outside, enjoy the screened lanai complete with sun shades, overlooking a fully fenced backyard with elegant iron fencing. Additional exterior features include an extended driveway, whole-home security camera system, and solar panels installed in 2022 for enhanced energy efficiency.Additional upgrades include a whole-home water softener system with reverse osmosis filtration in the kitchen, a dedicated garage outlet for an additional refrigerator or freezer, and numerous custom finishes that make this home truly move-in ready.With modern upgrades, exceptional attention to detail, and an ideal layout, this home offers the perfect combination of luxury, efficiency, and everyday comfort. Don't miss the opportunity to make this exceptional property your next home!

10750 Petrillo Way, Winter Garden

Courtesy of SUNSHINE LIFE REALTY LLC

$559,900
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

$420,000
3 Beds ⋅ 3 Baths ⋅ S5152170 MLS ⋅ Khovnania BLDG.
Welcome to this beautiful 2022 townhome located in the highly desirable Horizon West area of Winter Garden. This spacious residence features 3 bedrooms, 2.5 bathrooms, and approximately 1,732 square feet of thoughtfully designed living space. The open-concept floor plan offers a modern kitchen with ample cabinetry, a large island, and seamless flow into the dining and living areas, perfect for everyday living and entertaining. Upstairs, the primary suite includes a private bath and generous closet space, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of a two-car garage, low-maintenance living, and access to excellent community amenities. Ideally located near top-rated schools, shopping, dining, major highways, and world-famous attractions, this home offers the perfect combination of comfort, convenience, and lifestyle in one of Central Florida’s fastest-growing communities.

12042 Grandrose Alley, Winter Garden

Courtesy of MY REALTY GROUP, LLC.

$590,000
4 Beds ⋅ 3 Baths ⋅ O6417175 MLS
Welcome to your dream home! Built in 2020, this stunning two-story single-family residence perfectly blends modern design, comfort, and functionality. Featuring 4 spacious bedrooms, 2 full bathrooms, and 1 half bath, this home offers the ideal layout for both everyday living and entertaining. Step inside to discover an open-concept floor plan filled with natural light, contemporary finishes, and thoughtfully designed living spaces that create a warm and inviting atmosphere. The modern kitchen seamlessly connects to the main living and dining areas, making it perfect for gatherings with family and friends. The generously sized bedrooms provide comfort and privacy, while the primary suite offers a relaxing retreat after a long day. Conveniently located in a desirable area, this property combines accessibility, comfort, and modern living. Whether you're looking for your primary residence or a smart investment opportunity, this home is ready to exceed your expectations. Property have tenants living month by month.

15367 Gilligan Court, Winter Garden

Courtesy of PAK HOME REALTY

$599,000
4 Beds ⋅ 3 Baths ⋅ TB8472370 MLS
Welcome to this beautifully designed 2021-built 4-bedroom, 3-bathroom plus a bonus room corner-lot home offering space, style, and convenience all in one. From the moment you step inside, you’ll notice the high ceilings, large windows, and abundant natural light that enhance the home’s open and airy feel. The open-concept layout is perfect for modern living, with a spacious kitchen featuring modern appliances, ample counter space, and seamless flow into the living and dining areas — ideal for both everyday life and entertaining. Step outside to a paved backyard retreat, providing a low-maintenance outdoor space perfect for relaxing or gathering with guests. The rear-facing garage adds curb appeal while keeping the front exterior clean and welcoming. Situated on a desirable corner lot, this newer home offers the added benefit of HOA-maintained landscaping, giving you more time to enjoy the community amenities — including a community pool — while keeping monthly costs reasonable in this low-HOA neighborhood. Also included are solar panels, offering energy efficiency and potential long-term savings. Located approximately 3.4 miles (just minutes away) from the world-famous Walt Disney World Resort area, this home combines comfort, efficiency, and an unbeatable Central Florida location close to major attractions, shopping, dining, and entertainment. The area is served by well-rated schools, many graded 7+ out of 10. Don’t miss the opportunity to own a move-in ready, newer-construction home with space, efficiency, and convenience all wrapped into one!

16012 Micelli Drive, Winter Garden

Courtesy of ALIGN RIGHT REALTY LLC

$550,000
3 Beds ⋅ 4 Baths ⋅ A4660262 MLS
Disney fireworks views, single-story living, low HOA — just 3.9 miles from Disney. Welcome to Winding Bay in Winter Garden, where location, lifestyle, and long-term value come together in one beautifully maintained home. This pristine 3-bedroom, 3.5-bath residence with a flexible bonus room offers the perfect setup for everyday living, visiting guests, remote work, or a potential future sleeping space with proper modification and verification. From the moment you arrive, the home makes a statement with its brick-paved driveway, stone-accented façade, and inviting curb appeal. Inside, the bright open floor plan is designed for comfort and function, featuring a dedicated built-in desk area, an oversized mudroom, an adjacent laundry room, custom cabinetry, and generously sized guest suites. The heart of the home is the chef-inspired eat-in kitchen, complete with 42-inch soft-close cabinetry, quartz countertops, designer backsplash, vented range hood, built-in microwave, massive walk-in pantry, and an oversized island with seating for up to eight — ideal for entertaining, hosting family, or gathering after a day at the parks. The open dining and family room are filled with natural light and flow seamlessly to the custom-designed backyard, where you can relax and enjoy direct views of Disney fireworks from home — a rare and memorable feature that truly sets this property apart. Winding Bay offers a peaceful, pride-of-ownership atmosphere with no short-term rentals permitted, helping preserve the neighborhood feel while still keeping you minutes from Disney, dining, shopping, schools, and major conveniences. Residents also enjoy a community pool, dog park, and a low HOA of just $102/month. Move-in ready, meticulously maintained, and positioned in one of Winter Garden’s most desirable communities, this home is ideal for owner-occupants, Disney professionals, second-home buyers, or anyone seeking proximity to the magic without the noise, crowds, or rental turnover. Private showings available by appointment.

15456 Gilligan Court, Winter Garden

Courtesy of NEXTHOME CASA BELLA ELITE

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