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

16012 Micelli Drive, Winter Garden
$599,000
4 Beds ⋅ 3 Baths ⋅ O6450178 MLS
Virtually Staged. Welcome to 16012 Micelli Drive, a beautiful home built in 2021, ideally situated on a desirable corner lot in the Winding Bay community of Winter Garden, Florida! Featuring 4 bedrooms, 3 full bathrooms, and an additional versatile room, this thoughtfully designed home combines modern comfort, functionality, and style. From the moment you step inside, you'll appreciate the soaring ceilings, expansive windows, and abundant natural light that create a bright, open, and welcoming atmosphere. The spacious open-concept floor plan is designed for both everyday living and effortless entertaining. The kitchen features modern appliances, generous countertop space, and a seamless connection to the living and dining areas, creating an inviting space to gather and make lasting memories. Step outside to discover a beautifully paved backyard offering a low-maintenance outdoor retreat, perfect for relaxing, enjoying Florida's sunshine, or entertaining guests. The rear-entry garage adds convenience while preserving the home's attractive curb appeal. Located on a corner lot, this property offers even more reasons to fall in love with Florida living. Lawn maintenance is included in the HOA, giving you more time to enjoy your home and the community amenities, including a refreshing community swimming pool. The community also features a low HOA fee. An additional highlight is the home's solar panel system, offering the potential for increased energy efficiency and long-term savings. Location is another standout feature! Situated approximately 3.4 miles from the Walt Disney World Resort area, this home offers convenient access to Central Florida's world-famous attractions, shopping, dining, entertainment, and major roadways. Whether you're searching for a place to settle into your next chapter or a home designed for everyday comfort, 16012 Micelli Drive brings together thoughtful design, desirable amenities, and a fantastic Winter Garden location. Come discover the possibilities and imagine the next chapter of your story beginning here!

16012 Micelli Drive, Winter Garden

Courtesy of ALVES AND HOWELL REALTY

15411 Gilligan Court, Winter Garden
$514,000
4 Beds ⋅ 3 Baths ⋅ O6446141 MLS
Located in Horizon West, this 4-bedroom, 2.5-bath home features a first-floor bedroom, private outdoor entertaining space, and no carpet throughout. Set within Winding Bay and zoned for top-rated schools, the community offers parks, a playground, walking trails, a dog park, and a resort-style pool with a splash pad. Just minutes from Walt Disney World, residents enjoy nightly fireworks views and convenient access to Highway 429, Hamlin Town Center, Flamingo Crossings, premier golf courses, and a wide variety of dining and shopping destinations. No CDD. Low HOA.

15411 Gilligan Court, Winter Garden

Courtesy of REAL BROKER, LLC

10750 Petrillo Way, Winter Garden
$629,000
3 Beds ⋅ 3 Baths ⋅ O6441092 MLS
Move-in ready single-story home in Winding Bay, part of Horizon West in Winter Garden. Tile flooring, upgraded in 2025, runs throughout with no carpet anywhere. The open kitchen features an oversized island, custom range hood, upgraded cabinetry with crown molding, and under-cabinet lighting. The primary suite offers plantation shutters, dual sinks, a large walk-in closet, and an en-suite bath fully renovated in 2026 with floor-to-ceiling tile and a rain shower head. Two secondary bedrooms share a Jack-and-Jill bathroom. At the front of the home, a 12x17 flex room works as an office or fourth bedroom. Double sliding doors open to a screened lanai with sun shades and a fully fenced backyard, with views of Disney fireworks. Additional features include solar panels, a whole-home water softener, and a kitchen reverse osmosis system. The community offers a pool, park, and dog park, with convenient access to shopping, dining, and major roadways. Schedule your showing today!

10750 Petrillo Way, Winter Garden

Courtesy of KELLER WILLIAMS ADVANTAGE III

15009 Lebeau Loop, Winter Garden
$689,000
3 Beds ⋅ 3 Baths ⋅ O6427810 MLS
**Seller is Motivated ** Beautifully upgraded *POOL* home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home 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

15068 Lebeau Loop, Winter Garden
$639,000
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

14931 Lebeau Loop, Winter Garden
$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

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