Winding Bay Homes with Sidewalks Community Features

Winding Bay Homes with Sidewalks Community Features

Welcome to Winding Bay, a picturesque subdivision nestled in the heart of Winter Garden, Florida, in vibrant Orange County. This charming community is designed for those who appreciate the perfect blend of tranquility and accessibility, making it an ideal place to call home.

Winding Bay boasts a collection of beautifully crafted homes, each thoughtfully designed to cater to modern lifestyles. One of the standout features of this community is its commitment to walkability, with well-maintained sidewalks lining the streets. This not only enhances the aesthetic appeal of the neighborhood but also encourages an active lifestyle. Residents can enjoy leisurely strolls, morning jogs, or evening bike rides, all while soaking in the scenic surroundings and friendly atmosphere.

The community is surrounded by lush greenery and offers ample recreational spaces, including parks and playgrounds, making it perfect for families and outdoor enthusiasts alike. With its close proximity to Winter Garden's bustling downtown area, residents have easy access to a variety of dining, shopping, and entertainment options. The famous West Orange Trail is just a stone's throw away, providing miles of scenic pathways for walking, running, and cycling.

In Winding Bay, you'll find a welcoming community that values connection and engagement. Whether you're a first-time homebuyer or looking to settle down, this subdivision offers a unique blend of comfort, convenience, and charm. Come discover your dream home in Winding Bay, where every day feels like a vacation in paradise!

Newest Winding Bay Homes with Sidewalks Community Features

15032 Lebeau Loop, Winter Garden
$499,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code
Like-new and just five years young, this beautifully cared-for home showcases thoughtful upgrades and attention to detail throughout. Featuring 3 bedrooms, 2.5 baths, and a dedicated office space, the inviting layout offers room to live, work, and unwind. The open kitchen features a gas range, spacious walk-in pantry, and adjacent dining area, making everyday meals and entertaining effortless. Upstairs, the generously sized primary bedroom includes a walk-in closet with custom built-ins for exceptional organization. Enjoy your own private retreat in the fenced backyard, thoughtfully enhanced with maintenance-free landscaping. A two-car garage with an EV charger, tankless gas water heater, and water softener system add everyday convenience. Community amenities include a pool, three playgrounds, two dog parks, and community mailboxes. Conveniently located near Flamingo Crossings Town Center for shopping, dining, and primary care/ER services, as well as Disney, this meticulously maintained home offers comfort, convenience, and thoughtful details inside and out.

15032 Lebeau Loop, Winter Garden
10750 Petrillo Way, Winter Garden
$625,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code
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
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