A Post Office opened at Windermere in 1888. The Post Office closed in 1901, and reopened in 1911. Windermere was established as a residential development in 1889 and chartered in 1925.
During late 2007, the Town of Windermere filed a proposal to annex Isleworth and Butler Bay, both wealthy subdivisions. 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 unincorporated, but Butler Bay was annexed into Windermere, with over 90% of its residents approving annexation via a mail-in ballot.
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