The Town of Windermere is located in southwest Orange County fourteen miles southwest of Orlando, six miles southeast of Winter Garden, two miles south of Ocoee, and approximately six miles north of Walt Disney World.

Windermere is surrounded by sand bottom lakes. Lake Butler (the largest) is on the west, Lake Down on the east, and Lake Bessie on the southeast. By means of a system of canals, Butler, Down and six other lakes are connected to form what is known as the Butler Chain.