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 in the county, but Butler Bay was annexed into Windermere, with over 90% of its residents approving annexation via a mail-in ballot.

According to the United States Census Bureau, the town has a total area of 1.57 square miles (4.07 km²), of which 1.56 square miles (4.03 km²) is land and 0.015 square miles (0.04 km²), or 0.98%, is water.

The record high temperature in Windermere is 101 °F, which took place in 1998, and the record low temperature is 19 °F, which took place in 1985.

As of the census of 2013, there were 2,855 people, 784 households, and 591 families residing in the town. The population density was 1,688.2 inhabitants per square mile (654.0/km²). There were 723 housing units at an average density of 643.4 per square mile (249.2/km²). The racial makeup of the town was 95.68% White, 1.3% Black, 0.05% Native Americans, 2.00% Asian, 0.32% from other races, and 0.69% from two or more races. Hispanic or Latino of any race were 3.53% of the population.

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