[citation needed] 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.

[6] The Town of Windermere is part of the humid subtropical climate zone with a Köppen Climate Classification of "Cfa" (C = mild temperate, f = fully humid, and a = hot summer).

[7] As of the 2020 United States census, there were 3,030 people, 1,426 households, and 1,047 families residing in the town.

[12] As of the 2010 United States census, there were 2,462 people, 875 households, and 770 families residing in the town.

Windermere has a Town Manager / City Council form of government.

[14] In January 2014, the department's former chief, Daniel Saylor, was sentenced to eight years in prison for perjury.

He had lied to the court in order to protect a friend who was found guilty of raping children and sentenced to life in prison.

[17] The Floridan Aquifer is Windermere and Orange County's source of drinking and fire hydrant water, which is filtered naturally through hundreds of feet of sand and rock, and then treated by the Orange County Water Division.

[citation needed] In 2004, two roundabouts were installed downtown with the largest public works project in the town's history.

A third roundabout was completed in August 2010 at the intersection of Park Avenue and Maguire Road.

The Florida Midland Railroad, part of the Atlantic Coast Line Railroad, used to run just west of Main Street; there is now a large grassy area between Main Street and the dirt road (often called Dirt Main Street) that ran just west of the railroad.