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Among the Lakes

Windermere Town Hall

Isleworth Golf Community

Keene's Pointe

Isleworth Estate

Nestled among the spring-fed Butler Chain of Lakes, the cozy Town of Windermere, population 2,300, has emerged as the region’s new-money address of choice.

With Lake Butler on the west, Lake Down on the east and Lake Bessie on the southeast, Windermere is a verdant peninsula where 317 of 837 homes are on the water. Windermere, or at least the area surrounding it, is also home to some of Central Florida’s most upscale new communities.

But although they advertise Windermere addresses, most of these ritzy developments aren’t technically in Windermere, much to the chagrin of some locals who object to the alleged misappropriation of the town’s proud name.

In fact, Windermere itself is just is just 689 acres and consists largely of a laid-back retail district with a few mom-and-pop stores with a scattering of older homes lining sandy streets. Those streets remain unpaved to discourage traffic and prevent runoff from damaging the Butler Chain, which consists of eight pristine lakes connected by a canal system.

The lakes attracted one of Windermere’s first investors, Joseph Hill Scott. Scott’s son, Stanley, homesteaded the property and supposedly named it after Lake Windermere in England.

The railroad connected Windermere and Kissimmee in 1889, but freezes in 1894 and 1895 destroyed the town’s citrus industry. Little changed until 1910, when a pair of Ohio investors named D.H. Johnson and J. Calvin Palmer bought all the land they could piece together and formed the Windermere Improvement Company for the purpose of developing it.

The pair promoted “Beautiful Lakes of Pure Spring Water” and aimed their marketing at moneyed Northerners.

Although few who live here want to see the town change significantly, Windermere city officials are making concessions to the growth surrounding it. In 2006 the town completed a $2.5 million public works project – the largest in its history – to revamp the downtown area, bricking three blocks of Main and Frontage streets, expanding parking lots, replacing stop signs with roundabouts and generally upgrading its appearance.

And developer Kevin Azzouz, who in 2003 purchased much of the property in the business district, has talked about creating a town center, much to the consternation of those who like downtown’s unpretentious combination of shabby and chic. In fact, at this writing, Azzouz and city officials remain at odds over the proposed project.