Windermere was established in 1889 and chartered in 1925. During late 2007, the Town of Windermere filed a proposal to annex Isle worth 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, Isle worth remained in the county, but Butler Bay was annexed into Windermere, with over 90% of its residents approving annexation via a mail-in ballot.
Windermere has a Town Manager / City Council form of government. Five council members are elected at large for two-year terms with three running for election in odd years and two running for election in even years along with the mayor. Gary Bruhn has served as mayor for six consecutive terms since 2004.
Police services are provided by the Windermere Police Department. Fire rescue and emergency medical services are provided by Orange County Fire Rescue - Fire Station 35, which is located in Windermere. Postal services are provided by the Windermere Post Office. The Floridian 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
The schools include Windermere Elementary School and Gotha Middle School, Orange County Public Schools in Windermere, assigned based on the parent/guardian's home address. OCPS also provides school buses for local students.
Windermere is also home to Windermere Preparatory School, a private, coeducational PK-12 college prep school.
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 was 3.53% of the population.
In the town the population was spread out with 27.5% under the age of 18, 5.1% from 18 to 24, 25.8% from 25 to 44, 30.5% from 45 to 64, and 11.1% who were 65 years of age or older. The median age was 41 years. For every 100 females there were 104.2 males. For every 100 females age 18 and over, there were 96.3 males.
The median income for a household in the town was $88,809, and the median income for a family was $105,737. Males had a median income of $80,693 versus $37,321 for females. The per capita income for the town was $51,370. About 2.4% of families and 3.1% of the population were below the poverty line, including 3.0% of those under age 18 and 9.1% of those ages 65 or over.