Winding Bay Real Estate

Winding Bay Real Estate

Welcome to Winding Bay, a picturesque subdivision nestled in the heart of Winter Garden, Florida, located in the vibrant Orange County. This charming community perfectly balances serene suburban living with convenient access to urban amenities, making it an ideal choice for families, retirees, and everyone in between.

Winding Bay is characterized by its beautifully landscaped streets, adorned with mature trees and lush greenery, creating a tranquil atmosphere that invites residents to enjoy the great outdoors. The well-designed homes in this neighborhood boast a variety of architectural styles, each reflecting a unique charm while providing modern comforts. With spacious layouts and thoughtful designs, these homes cater to diverse lifestyles, whether you’re looking for a cozy retreat or a family-friendly haven.

One of the highlights of Winding Bay is its proximity to the stunning downtown Winter Garden, where you can explore a vibrant mix of shops, restaurants, and local markets. Enjoy leisurely strolls along the West Orange Trail, a scenic pathway perfect for biking, walking, or jogging. The area is also home to top-rated schools, parks, and recreational facilities, ensuring that residents have access to excellent educational and leisure opportunities.

For those who crave adventure, Winding Bay is just a short drive from the world-renowned attractions of Orlando, including theme parks and entertainment hubs. With easy access to major highways, commuting to nearby cities is a breeze.

Discover the charm and convenience of Winding Bay, where community spirit thrives and every day feels like a vacation. Come join us and experience the perfect blend of comfort and excitement in this delightful Winter Garden neighborhood!

Newest Listings in Winding Bay

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
$629,000
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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