Windsor Hill Homes for Sale
Windermere's original guard-gated estate neighborhood with pools, parks, and Butler Chain of Lakes proximity.
Homes for sale in Windsor Hill
Inside Windsor Hill
Windsor Hill is a gated residential community in Windermere, Florida, established in 1989 and developed through 2013 in Orange County. The subdivision comprises approximately 109 estate homes situated on expansive half-acre to one-acre lots, featuring traditional architecture and modern upgrades. Homes range from 2,400 to 9,600 square feet and typically offer 4 to 7 bedrooms with private swimming pools and screened lanais, targeting affluent buyers seeking refined estates near Orlando attractions.
The community operates as a guard-gated enclave with 24-hour security, in keeping with Windermere’s low-density residential character. HOA fees range from $1,050 to $1,335 monthly, covering landscaping, roadway maintenance, insurance, clubhouse amenities, and common area management. The community park includes tennis courts and a children’s playground under mature shade trees. Residents benefit from proximity to the Butler Chain of Lakes for boating and water sports, as well as quick access to Walt Disney World, Universal Studios, and downtown Orlando via the Florida Turnpike, I-4, and area expressways.
Windsor Hill is zoned for short-term rental, making it attractive to real estate investors seeking vacation home returns. The nearby Grove Shopping Center, a public high school campus, and medical facilities at AdventHealth provide everyday conveniences. The neighborhood maintains a tranquil residential character while remaining within urban reach of employment centers and entertainment.
Windsor Hill addresses are assigned elementary, middle, and high school campuses by Orange County Public Schools. School assignment should be confirmed independently before purchase, as zone boundaries can change. The neighborhood’s appeal rests on privacy, security, lakefront recreation, and proximity to the Orange County Public Schools campuses that serve the broader Windermere area.
The facts
Frequently asked
What is the price range for homes in Windsor Hill?
Windsor Hill homes typically range from approximately $700,000 to $7.5 million, with recent sales in the mid-$750,000 range. Home prices reflect lot size, square footage, upgrades, and proximity to the Butler Chain of Lakes. For current market listings and specific property valuations, contact a Market Connect Realty agent specializing in Windermere estates.
Is Windsor Hill a gated community?
Yes, Windsor Hill is a private, guard-gated community with 24-hour security access and personnel. All residents and guests must present photo identification and confirmation to enter, providing a secure residential environment. The gated enclosure is one of Windermere's defining luxury features for discerning homeowners.
What schools are zoned for Windsor Hill?
Windsor Hill students are zoned to elementary, middle, and high school campuses within Orange County Public Schools. School zones can shift, so confirm current assignments independently before purchasing. Market Connect Realty agents can provide verified zone documentation for specific properties.
What are the HOA fees in Windsor Hill?
Monthly HOA fees in Windsor Hill range from $1,050 to $1,335, depending on property type and included services. These fees cover landscaping, common area maintenance, clubhouse amenities, roadways, sidewalks, insurance, and 24-hour guard-gated security. Contact the Windsor Hill Homeowners Association for a detailed fee schedule and amenity coverage breakdown.
What amenities does Windsor Hill offer?
Windsor Hill amenities include a community park with tennis courts, children's playground under mature shade trees, walking and biking trails, and access to nearby golf courses and the Butler Chain of Lakes. Properties typically feature private swimming pools and screened lanais. The neighborhood emphasizes outdoor recreation and security rather than resort-style clubhouse facilities.
How many homes are in Windsor Hill?
Windsor Hill contains approximately 109 estate homes spread across half-acre to one-acre residential lots. The subdivision features various architectural styles with homes ranging from 2,400 to 9,600 square feet, primarily developed between 1989 and 2013 by multiple luxury builders.
Is short-term rental allowed in Windsor Hill?
Yes, Windsor Hill is zoned for short-term rental, making it attractive for vacation home investors seeking Orlando-area rental income. Owners can rent properties to tourists, though specific HOA rental restrictions and property manager requirements should be verified with the association before purchasing for investment purposes.
What year was Windsor Hill developed?
Windsor Hill was originally developed beginning in 1989 and continued building through 2013, spanning approximately 24 years of development. The original homes were constructed by various luxury home builders, with many properties subsequently upgraded with modern amenities, new exteriors, and contemporary kitchen features.