About Windermere Active Adult Communities
Windermere offers an exceptional active adult lifestyle for those 55 and over seeking resort-style living, social engagement, and low-maintenance homes in Orange County. While the Town of Windermere itself is a historic, lakefront enclave on the Butler Chain of Lakes rather than a planned 55+ destination, retirees are drawn here for the brick streets and English-village character of the downtown core, the boating and waterfront lifestyle, and the proximity to Central Florida's largest concentration of new active adult construction just minutes away in Horizon West and Winter Garden. Active retirees who choose the Windermere area typically want both — the quiet luxury of waterfront living on the Butler Chain or in established master-planned neighborhoods like Summerport, Lakes of Windermere, and Windermere Trails, plus easy access to dedicated 55+ amenities a short drive away. The community's active adult neighborhoods provide residents with the perfect combination of recreation, relaxation, and like-minded neighbors.
The closest dedicated 55+ community is Del Webb Oasis, a Pulte-built gated boutique community on Hartzog Road in Winter Garden near the Horizon West border, featuring a 12,000 square foot clubhouse with zero-entry resort pool, pickleball courts, fitness center, lifestyle director, and single-family and villa floor plans within roughly 10–15 minutes of downtown Windermere and the Walt Disney World resort. Additional age-targeted options nearby include Overture Hamlin in Horizon West and Arya at Windermere — a 55+ rental community in adjacent Ocoee, which uses the Windermere name despite the address — while retirees comfortable in non-age-restricted neighborhoods can pair a single-story home in Dr. Phillips, Gotha, or guard-gated Keene's Pointe with the area's golf, dining, and healthcare access through local restaurants, golf and recreation, and the Orlando Health Medical Pavilion Summerport on CR 535. Whether you're seeking a villa with golf course views, a coach home with maintenance-free living, or a single-family home in a gated 55+ community, Windermere active adult communities offer a variety of home styles, amenities, and price points to suit different retirement lifestyles and preferences.
David Myers
