While Windermere, Florida, best known for its natural beauty, may be synonymous with celebrities and mansions, its roots and community spirit run much deeper than that. It may cultivate and project an affluent, prestigious image, but Windermere is old Florida, striving to maintain its small town ambiance, philanthropic attitude and family-friendly atmosphere. Those that have lived in Windermere long enough remember its citrus grove and simple winter vacation cottage roots. Though the orange groves and lake shacks may have given way to sprawling estates and rolling green golf courses, what has permeated the oak-lined dirt roads that wind past generations-old homes to the clear, cypress-kneed and sandy-bottomed lakes, is the insular sense of community and devotion of its residents.
Windermere’s humble roots were planted in the 1870s, following an influx of English settlers to Orange County and the issuance of homestead certificates to several individuals lured by the lakes and the promise of prosperity they perceived in the ideal location for growing the citrus tree. The sleepy land was beginning to develop an identity, when in 1885 the name Windermere was bestowed upon it by an Englishman and Oxford graduate. He named it after the famous lake and town in the United Kingdom, upon homesteading 160 acres for citrus grove cultivation. 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 again 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. A year later, 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 and gentle spurts when both Martin Co. (currently Lockheed Martin) executives discovered it in the late 1950s and early 60s, and Disney executives in the late 1960s and early 70s.
Today, the isthmus on the Butler Chain of Lakes maintains its small-town character with not only its unpaved dirt roads, but with its modest town center strip on Main Street of quaint shops, cafes, a real estate office and other resident catered to business, as well as, its town manager/city council form of government. Windermere real estate consistently ranks among the most expensive and desired in America. Windermere remains a good choice for families earning Neighborhood Scout’s distinction of “Number One Top Choice Town for Families with Children in the Sunshine State” in large part due to its good public schools, low rate of crime and large population of college-educated, home-owning adults. And of course, 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 eleven 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 and championship fishing opportunities.
Approximate Distance to:
Orlando International Airport: 20 miles
Universal Studios, Florida: 6 miles
Walt Disney World Resort: 10 miles
Downtown Orlando: 12 miles