Windermere History

Windermere Florida was established in 1889 and chartered in 1925. The Town’s oldest structure is a schoolhouse that was built in the late 1800s. The schoolhouse is currently located on 7th Avenue and will be relocated to Town Square behind Town Hall between the library and the Community Room, and will be restored as an authentic representation of a one room schoolhouse in the late 1800s.

Windermere is a town in Southwest Orange County Florida and is located 14 miles Southwest of Orlando. Windermere is adjacent to Winter Garden, is approx two miles south of Ocoee and is minutes away from the Walt Disney World Resort. 

Windermere is perfectly located South West of Orlando and is convenient to all of the area attractions.  With  some of the most affluent water front real estate in Central Florida located in Windermere, the proximity to high end shopping options is sure to please the most discerning tastes. Orlando's most luxurious mall, the Mall at Millenia a mere 6 miles away.

Windermere is known as the Town Among the Lakes and is surrounded by beautiful sand bottom lakes. Lake Bessie on the southeast, Lake Butler  is on the west and Lake Down is on the east. By means of a system of canals, Butler, Down and six other lakes are connected to form what is known as the Butler Chain. The Butler Chain of Lakes is comprised of Lake Butler, Lake Louise, Lake Isleworth,  Lake Down, Little Lake Down, Wauseon Bay, Lake Chase, Pocket Lake, Lake Tibet, Lake Sheen, and Fish Lake.

The Butler Chain of Lakes offer an abundance of on-water activities including championship fishing, pro golf tournaments, lake cruises, boating, canoeing and kayaking.  The abundance of sand bottomed lakes in this region gives Windermere lake front real estate incredible value. Beautiful large trees and lakes abound, the  outdoors invites you to relax and play in the scenic natural wonder that is Windermere.

Windermere is a town full of wonderful historic charm. The quaint city center remains well preserved with magnificent shops, cafes and other venues located downtown. The small community is one of best places to live for families and has been voted "Neighborhood Scout's" top choice town for families with children in all of Florida.  Residents take advantage of the town's amenities like the local country club and the high shopping if the beautiful outdoors is not calling to them.

Neighborhoods in the area are relatively new and the demographics is middle to upper class. The homes are larger than the average suburban home. If you are seeking a custom luxury home, Windermere is a perfect place to look. 

Windermere real estate is some of the most expensive and sought after real estate in Central Florida. The Guard Gated Community of Isleworth in Winderemere features clay tennis courts, a golf course designed by Arnold Palmer, the 89,000-square-foot Isleworth Country Club, a wellness center and outdoor sculptures.

Below you can view the newest Homes for Sale and Real Estate Lisitngs in Windermere Florida.