Windermere FL History

  • Town Hall
  • Old Police Department
  • Windermere FL Library

The Windermere FL History

Windermere Florida’s history is an interesting one. Windermere, like many of the homes here in the greater Orlando FL area was founded over a hundred years ago. Does that matter? Well, a little depending on who you ask and your perspective. One thing for sure either the history, the environment or both have definitely helped sculp the current lifestyle of this small town “among the lakes”. Everyone should take a drive down Main Street in Windermere FL.

Windermere FL

Prior to 1564 the area of Windermere was occupied by the Timucuan Indians who occupied much of Central FL into Southern Georgia. It was in 1564 that the the Spanish who originally landed around St Augustine to the north in 1513 had made it to this area.

The United States then began to offer 160 acres to settlers who would move to this area, cultivate 5 acres and erect a cabin on the land. Imagine that, paid to move to this location.

Skipping forward a few hundred years Florida becomes the 27th state on March 3, 1845. In 1885 an English gentleman named Stanley Scott purchase 160 acres in Windermere. His son Dr. Stanley Scott was later given credit for actually naming the area Windermere most likely after Lake Windermere which is the largest natural lake in England.

The name could have also been from the town of Windermere which is not far from Lake Windermere. Some sources say the town was officially named by John Dawe when he laid out the town and platted it for three owners in 1887. The town of Windermere in the United Kingdom actually was named after the lake.

The Railroad

The railroad arrived in Windermere and the first schoolhouse opened in 1887. The post office followed in 1888. The city was officially established as a residential development in 1889. Windermere was then well on its’ way and received its' charter to incorporate in 1925.

There are more notable names in Windermere FL history. Those names are Joshua and Sydney Chase and RD Keene. Sydney and Joshua Chase owned a citrus grove which later became Isleworth. They referred to their grove as “the isle of worth” because the many lakes helped it be resistant to cold snaps and freezes.

The Chase family’s contribution to Windermere is one of the reasons you drive down Chase Road. In 1984 the family sold Isleworth to Arnold Palmer. Just a few years later in 1993 Tavistock purchased the lands and developed the community and property.

RD Keene is in the Florida Citrus Hall of Fame. He also owned the land that later became Keenes Pointe. The large park on Chase Road which bears his name is just a token compared to his contribution to both Winter Garden FL and Windermere FL history.

Go Ahead Move To Windermere FL

Windermere is now a much more stable area. Its’ early years were definitely affected by some hard freezes and challenges one faces when growing oranges. Now those days are long gone and Windermere primarily markets a lifestyle to those who can afford it.

Thank you for visiting this site and reading about our fine city. Visit the local Windermere FL library for more information on Windermere FL history.

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