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Windermere FL, Homes For Sale, History of Windermere, Orlando

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Windermere Florida, History of Windermere, Orange County

From the majestic live oaks dripping with Spanish moss to the pristine fresh water Butler Chain of Lakes, Windermere Florida is steeped in history. Established in 1889 and chartered in 1925, Windermere has maintained its small town Florida charm, while making all the necessary advancements to be seen as a thriving modern city. One of the more notable moves in this direction came in 2007 when Windermere attempted to annex two affluent communities bordering its city limits, Isleworth and Butler Bay. This attempt was met with resistance from Orange County which stood to lose millions in property tax revenues as a result of the proposed annexation. The result was the annexation Butler Bay which was approved by 90% of Butler Bay’s population. Isleworth remains under Orange County jurisdiction.

Windermere, FL, Historic Buildings, Historic Homes For Sale

With many historic buildings and a rich history, Windermere has many times been referred to as the Williamsburg of Florida. The Windermere Town Hall occupies a restored 1890s school house, and the downtown area is home to several historic buildings including the Cal Palmer Memorial Building. Cal Palmer was one of many historic figures who molded the history of Windermere by co-founding the Windermere Improvement Company with his partner John Calvin Palmer which was responsible for developing and selling of property around Windermere.

Wendy Morris is the only name you need to know when it comes to any Florida real estate transaction, especially historic homes for sale. Contact us today at (407) 575-5392 for all your Orlando, Windermere or Florida real estate needs.




All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 2/21/26 8:20 PM) |

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Winter Garden, Florida 34787

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