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Windermere is an incorporated town in Orange County, Florida, in the Orlando metropolitan area, and its motto is 'Among the Lakes.'

Windermere was platted in 1887 by John Dawe, an Englishman who named the community after Lake Windermere in England's Lake District.

The Town of Windermere was officially incorporated on February 2, 1925, and it celebrated its 100th anniversary on February 2, 2025, which the Florida Senate recognized as 'Town of Windermere Day.'

The town sits on a narrow isthmus between Lake Butler and Lake Down, on the Butler Chain of Lakes, and serves as the shortest road crossing between the east and west sides of the chain.

The Butler Chain of Lakes was the first lake system in Florida designated an Outstanding Florida Water by the Florida Department of Environmental Protection, a distinction it earned in 1985.

Windermere had a population of 3,030 at the 2020 census — up from just 153 residents in 1930 and 596 in 1960.

Recent Census Bureau survey estimates put the town at roughly 1,180 households, with a homeownership rate of about 96% and a median home value near $987,500, making it one of Florida's most affluent small towns.

The incorporated town covers less than three square miles, and most homes with a Windermere mailing address actually lie in unincorporated Orange County outside the town limits.

In a long annexation fight with Orange County, the wealthy Butler Bay subdivision joined Windermere after more than 90% of its residents approved in a mail-in ballot, while Isleworth — one of America's most famous golf communities — remained unincorporated.

Despite the shared name, the town of Windermere is not within the attendance boundaries of Windermere High School, which opened in 2017 in the nearby unincorporated Lake Butler area, and Windermere Preparatory School is likewise located just outside the town.