Windermere
Prestigious lakefront living wrapped in natural beauty, old-Florida charm, and an unmatched sense of serenity.
Welcome to Windermere
Nestled among the glittering waters of the legendary Butler Chain of Lakes just west of Orlando, Windermere is Central Florida's most prestigious address — an enclave of serene beauty, old-Florida charm, and world-class luxury that has long captivated discerning buyers from around the globe. The Town of Windermere is overflowing with history, charm, and an "old town" sense of family, with 11 community parks, community docks, tennis courts, rowing clubs, nature trails, and award-winning restaurants.
Known for its pristine lakefront estates and celebrity residents, Windermere is Central Florida's most prestigious address for luxury homes, with magnificent properties along the renowned Butler Chain of Lakes offering architectural masterpieces ranging from Mediterranean villas to contemporary waterfront estates with private docks.
What to Love
The Butler Chain of Lakes — 13 interconnected lakes offering world-class boating and recreation
Home to legendary residents including Shaquille O'Neal and Tiger Woods
Timeless small-town character paired with unrivaled luxury living
Local Lifestyle
The town hosts a variety of events throughout the year, including food truck nights, farmers' markets, and holiday parades, fostering a close-knit community spirit. Despite its prestige, Windermere maintains an unhurried pace — notably, the town has even resisted paving its side roads as a deliberate choice to preserve the area's natural beauty and charm.
Dining, Entertainment & Shopping
The town's quaint downtown core is dotted with family-owned shops and charming cafes. Minutes away, residents find upscale dining, boutique shopping, and easy access to Orlando's world-class entertainment. The Butler Chain of Lakes itself creates an exclusive boating community that rivals any coastal destination, with crystal-clear waters that remain consistently clean and beautiful throughout the year.
Things to Do
The Butler Chain of Lakes is one of the few pristine chains of lakes remaining in Central Florida and is a haven for fishing, boating, wakeboarding, and waterskiing, while the nearby Tibet Butler Nature Preserve offers 483 acres of untouched wetlands, pine forest, and lakeshore. The Isleworth Golf & Country Club and the Jack Nicklaus-designed Golden Bear Club are among the area's world-class golf offerings.
Schools
Windermere is served by Orange County Public Schools, with several highly rated campuses in the area. Top private school options include the acclaimed Windermere Preparatory School, ranked among the best in Florida.