Windermere is a town in Orange County, Florida, in the United States. As of the 2000 census, the town population was 1,897. According to the U.S. Census Bureau's 2006 estimates, the town had a population of 2,019. It is expected that the 2010 census will show the town with almost 3000 people. It is part of the Orlando–Kissimmee Metropolitan Statistical Area.
Windermere was established in 1889 and chartered in 1925.
During late 2007, the Town of Windermere filed a proposal to annex Isleworth and Butler Bay, another wealthy subdivision. This was met with extensive debate from town residents and an objection from Orange County, which stood to lose millions of dollars of property tax revenue. After lengthy discussions, and battles with the county, Isleworth remained in the county, but Butler Bay was annexed into Windermere with over 90% of its residents approving annexation via a mail in ballot.