Lakefront luxury and small-town charm in one of Central Florida’s most prestigious communities. Discover Windermere FL real estate.
Located between the sparkling Butler Chain of Lakes, Windermere is a serene and upscale town known for its stately homes, tree-lined streets, and exclusive lifestyle.
Just minutes from the attractions of Orlando, Windermere offers a rare blend of privacy, prestige, and proximity — making it one of the most sought-after communities in Central Florida for luxury homebuyers, families, and professionals.
Whether you're drawn to waterfront estates, gated golf communities, or walkable historic neighborhoods, Windermere has it all.
With A-rated schools, charming downtown shops, and a strong sense of community, it’s no wonder this area continues to attract discerning buyers from around the world.
Stunning lakefront estates on the Butler Chain of Lakes
Gated golf communities like Isleworth and Keene’s Pointe
Top-rated public and private schools
Quaint downtown with shops, cafés, and a weekly farmers market
Easy access to Disney, Downtown Orlando, and major highways
Living in Windermere means embracing an elevated lifestyle with a relaxed pace. Residents enjoy peaceful mornings on the water, afternoons spent boating or golfing, and evenings dining with neighbors in one of the town’s cozy restaurants or lakefront estates.
This town draws high-net-worth individuals, professionals, and families who value privacy, quality schools, and a true sense of place. It’s where Orlando Magic players, CEOs, and long-time locals come together in a community that feels like home.
Windermere may be quiet, but it’s full of culinary and cultural gems:
Feast BBQ, Yellow Dog Eats, and Paloma Coffee Co. are local favorites
The Grove at Windermere and nearby Winter Garden Village offer upscale shopping
Weekend brunches, food truck nights, and outdoor wine tastings bring the community together
Just 15 minutes to Restaurant Row in Dr. Phillips and Disney Springs for fine dining
Whether you want intimate lakeside dining or vibrant city options, Windermere puts it all within reach.
There’s something for everyone in Windermere:
Boating, paddleboarding, and fishing on the Butler Chain of Lakes
Golf at prestigious clubs like Isleworth and Golden Bear Club
Attend the Friday Farmers Market or seasonal events in the historic downtown
Walk, bike, or run the tree-canopied trails and residential streets
Explore nearby theme parks, just 20 minutes away
Residents love Windermere for its balance of nature, luxury, and community connection.
Windermere is home to some of the top schools in Central Florida, both public and private:
Windermere Elementary
Windermere High School – highly rated public school
Windermere Preparatory School – private PreK–12 with IB curriculum
Foundation Academy and The First Academy – nearby private options
The Windermere real estate market is one of the most prestigious in Florida, offering luxury estates, custom-built homes, and golf course properties. Whether lakefront or within a gated community, Windermere homes are known for their spacious lots, architectural excellence, and elevated lifestyle.
Inventory ranges from classic mid-century homes in the historic district to $10M+ estates in exclusive enclaves like Isleworth and Chaine du Lac.
If you're searching for luxury homes in Central Florida, Windermere tops the list. Common features include:
Private docks and lakefront access
Home theaters, wine cellars, and smart home systems
Grand outdoor entertaining areas with summer kitchens and infinity pools
Gated entries, long driveways, and lush landscaping
These homes offer privacy, prestige, and premium living, all minutes from Orlando’s best attractions.
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