About Windermere Gated Homes

Windermere gated homes

Windermere offers an attractive gated community lifestyle for those seeking enhanced security, privacy, and exclusive amenities in Orange County. Sitting on a peninsula surrounded by the Butler Chain of Lakes, Windermere is home to two of Central Florida's most recognized guard-gated communities — Isleworth and Keene's Pointe — anchoring a roster of private neighborhoods that have drawn professional athletes, executives, and high-net-worth families for decades. The town's deliberate small-scale character, brick streets, and proximity to Walt Disney World, top-rated Orange County schools, and the upscale dining scene in adjacent Dr. Phillips create an unusual combination of seclusion and access. The community's gated homes provide residents with the perfect combination of safety, prestige, and resort-style living.

Windermere's gated communities span the full luxury spectrum, from the ultra-exclusive 600-acre Isleworth with its Arnold Palmer–designed private course and 24-hour manned security, to Keene's Pointe, where roughly 1,067 custom homes across 14 villages surround the Jack Nicklaus signature Golden Bear Club with direct Butler Chain access. Smaller boutique enclaves include Casabella, a 79-homesite Toll Brothers community of half-acre estates, Lake Butler Sound on the lake's southwest shore, Tildens Grove adjacent to The Grove at Isleworth, and lakefront communities like Bellaria on Lake Burden and Chaine Du Lac directly on the chain. More accessible price points are available in resort-style master-planned communities such as Glenmuir, Reserve at Belmere, and Waterstone, which offer guarded entry, community pools, and fitness amenities at a fraction of the entry cost of the signature golf communities. Whether you're seeking a family-friendly neighborhood with pools and playgrounds, a golf course community with country club amenities, or a luxury estate with waterfront views, Windermere gated homes offer a variety of styles and price points to suit different lifestyles and preferences.