Windermere is a town in Orange County, Florida, in the United States. As of the 2010 census, the town population was 2,462. It is part of the OrlandoKissimmeeMetropolitan 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, a 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.