Windermere Florida is a gem amongst central Florida communities. The area referred to as Windermere is Located between Orlando and Walt Disney World, in the southwest section of Orange County. This area surrounds the quiet little Town of Windermere and has over 8000 homes. While the Town of Windermere has about 1100 homes and businesses. There are actually only about 2850 residents that live in the Town of Windermere. Many subdivisions that add the many homes to the area are not actually in the town limits. Some examples of these are: Isleworth, Keene’s Point, Lake Butler Sound, Summerport, and Belmere. These and other neighborhoods boasting private guard gated neighborhoods, golf courses, and lake front properties add a tremendous amount of real estate value to this area. These highlights and the Central Florida climate make Windermere one of the best communities in the country.
The motto of “Among the Lakes” is a true depiction of this areas prime location. The Town of Windermere is an isthmus surrounded by the Butler chain of Lakes. The Windermere name then continues to encompass most of the surrounding areas around the lakes. The Butler Chain of Lakes is made up of 11 lakes (Lake Down, Little Lake Down (Wauseon Bay), Lake Butler, Lake Louise, Lake Isleworth (Lake Palmer), Lake Tibet-Butler, Lake Chase, Lake Blanche, Lake Sheen, Lake Pocket, Fish Lake). One lake that is in the town but not connected to the chain is Lake Bessie. There are additional lakes that also share the Windermere address even though they are not in the town limits and are not connected to the Butler Chain of Lakes. Some of these are Lake Crescent, Lake Whitney, Lake Rhea, Lake Burden, Lake Sawyer, Cypress Lake, Lake William Davis, Lake Cawood and Lake Speer. Today this area is well known for its lakes and real estate, but that wasn’t always the case. In the late 1800’s this area was home to very few settlers until the Florida Midland Railroad came through in 1887. John H. Dawe an executive of the railroad laid out a small village. He named it Windermere after his home region in England which had lakes. He built a depot for the railroad and home for himself. The railroad went from Longwood to Kissimmee and became a preferred settlement for northerners who built seasonal homes. The following year the first post office in Windermere was established and soon after the reputation of the areas quality citrus-growing area was known.
Brothers, Sydney and Joshua Chase, purchased a large citrus tract that is now known as Isleworth. However, after only 2 short years, there was a winter freeze that virtually wiped out the citrus industry. Many land owners lost their property to foreclosure and left causing even the post office to shut down. Properties through the early 1900’s changed hands at fire sale prices and through tax sales. Then two Midwesterners, J.C. Palmer and Dr. J. Howard
Johnson, who were looking to take advantage of land values in Florida, went fishing on the Butler Chain of Lakes. They knew that Windermere was the place to call home after just a few days of fishing. With clear water lakes, well established timber, and the citrus trees coming back to bier fruit, they purchased about 2,000 acres. They formed the Windermere Improvement Company to develop and promote their property. Northerners built houses and shops and even a resort hotel in 1938 called the Pine Tree Inn. A building was built around 1923 for the Women’s Club and later was moved and became the Town Hall.