Windermere, Florida

Main Street Windermere

Windermere was founded on May 5, 1915, when 110 acres of land situated between James Avenue on the north, Lamar Avenue to the south, Main Street to the west, and 5th Street to the east, were auctioned off and incorporated under the council-manager form of government. In 2014, Windermere had a population of 2,503.

Windermere itself is just 689 acres and consists largely of a retail district with a “classic” feel and 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, an English clergyman who in 1885 bought 150 acres. Scott’s son, Stanley, homesteaded the property and supposedly named it after Lake Windermere in England.

By 1889, the Florida Midland railroad made its way through, connecting Sanford with Kissimmee and the Windermere town plat recorded. And prosperous it was, until the great freeze of 1894-1895 hit, devastating Windermere residents, who were unable to withstand the losses and the property foreclosures that followed. The Windermere residents moved away, slowing development until 1911 when two men from Wauseon Bay, Ohio, Dr. J.H Johnson and J. Calvin Palmer, rediscovered the sleepy town of Windermere and fell under its spell. The pair purchased roughly 2,000 acres in and around the town, and birthed the Windermere Improvement Company to both market and develop the land. Under vision and leadership, Windermere began to grow.

By 1924, wealthy northerners had bought land and lots, planted groves, created a board of trade, built houses and stores, a railway platform and new train depot, a sawmill, and a school house and a church. They also opened a resort hotel and restaurant, brought in telephone lines and tourists, and completed an asphalt road.

In 1925, Windermere was incorporated into a town and the Windermere Improvement Company dissolved. Steady growth occurred until Windermere experienced a population boom post World War II, roughly doubling the number of town occupants  when both Martin Co. (now Lockheed Martin) executives discovered it in the late 1950s and early ’60s, and Disney executives in the late 1960s and early ’70s.

Today, this community on the Butler Chain of Lakes maintains its small-town character with unpaved dirt roads to discourage traffic, and a modest town center on Main Street consisting of quaint shops, cafes, and other businesses. Windermere real estate consistently ranks among the desired in America and is a terrific choice due to its good public schools, low crime rate and large population of college-educated, home-owning adults.

Topping the list of desirability factors is the Butler Chain of Lakes, which remains one of the few clean water systems left in Central Florida. Consisting of 11 lakes linked together by natural waterways and man-made canals in a 10-mile chain are Lake Butler, Lake Louise, Lake Isleworth, Lake Down, Little Lake Down, Wauseon Bay, Lake Chase, Pocket Lake, Lake Tibet, Lake Sheen and Fish Lake, offering year-round water activities.

Interested in building a custom home in Windermere, Florida? Feel free to speak with one of the best home builders in Orlando, Budron Homes, about any questions you may have. Budron Homes is here to serve you and make sure your custom home is the home of your dreams. Call us today at (407) 347-0701 for a free consultation. Budron Homes is rated A+ with the BBB of Central Florida and is a 2015 Parade of Homes winner.

windermere