Windsor Hill
Nestled in the scenic heart of Windermere, Florida, Windsor Hill offers a tranquil and family-friendly setting with approximately 109 homes. This desirable neighborhood provides a perfect balance of peaceful living and convenient access to top attractions.
Spacious, Custom Homes
Built between 1990 and 2013, Windsor Hill features single-family homes that range in size from 2,400 to 9,600+ sq. ft., offering 4 to 7 bedrooms and 2 to 7+ bathrooms. The homes reflect various architectural styles and sizes, many showcasing modern upgrades and fresh exteriors.
Beautiful kitchen upgrades
Enclosed lanais with pools for year-round enjoyment
Expansive owner suites creating a blend of comfort and luxury
Well-manicured lots ranging from ½ to 1 acre
Community Amenities
Community park perfect for family gatherings
Tennis courts for recreation
Children’s playground
Prime Location & Convenience
Located just off Windy Ridge Road in Windermere, Windsor Hill offers easy access to Downtown Windermere, Winter Garden, and Restaurant Row. With grocery stores, retail shopping, and entertainment within a 10-mile radius, residents enjoy both peaceful living and proximity to daily conveniences.
Windsor Hill provides seamless access to major roadways including the Florida Turnpike, I-4, and the 408 & 429 expressways, making it easy to explore Orlando’s best attractions, such as Walt Disney World, Universal Orlando Resort, and SeaWorld.
For those looking to explore even more, International Drive, Orlando International Airport, and nearby beaches are all just a short drive away.
Windsor Hill at a Glance
Location: Windy Ridge Rd & Windsor Hill Dr
Surrounding Lakes: Butler Chain of Lakes
Number of Homesites: 94
Year Built: 1990 – 2013
Square Footage: 2,400 – 9,600+
HOA: Yes
Community Amenities: Community Park, Tennis Courts, Children’s Playground
Top-Rated Schools
Thornebrooke Elementary School (Pre-K – 5th) – 1.5 miles
Gotha Middle School (6th – 8th) – 1 mile
Olympia High School (9th – 12th) – 1 mile
Shopping & Dining Nearby
The Grove (Publix & Shops) – 2 miles
Winter Garden Village Shopping Center – 7 miles
Historic Downtown Winter Garden – 8 miles
Downtown Windermere – 3 miles
Restaurant Row – 6 miles
The Mall at Millenia & BJ’s Wholesale Club – 7 miles
Downtown Orlando – 12 miles
Parks & Recreation
Walt Disney World Resort – 10 miles
Gotha Park – 2 miles
Isleworth Golf & Country Club – 4 miles
MetroWest Golf Club – 4 miles
Dr. P. Phillips YMCA Family Center – 5 miles
Nearby Healthcare Facilities
Orlando Health Health Central Hospital – 4 miles
Windsor Hill offers a blend of spacious homes, a convenient location, and excellent amenities, making it the ideal community for those seeking the best of Windermere living.

