The History Of Windermere


A city in West Orlando, Windermere is populated by nearly 3,500 residents. It’s known for luxury lakefront homes and a quiet, peaceful vibe. It has also been home to many famous residents, including Stranger Things actress Millie Bobby Brown, Hall of Fame professional baseball player Ken Griffey Jr., and professional golfers Tiger Woods and Bubba Watson.


Location, Location, Location

Windermere is located in one of the best spots of the city, offering a balance of city-living amenities and small-town charm and quality of life. Another plus for many families, it’s a short 20-minute drive to Walt Disney World and Universal Studios.


More specifically, Windermere is situated on an isthmus between several lakes in the Lake Butler chain, including Lake Butler, Lake Down, and Lake Bessie. It's very fitting, then, that the town slogan is “among the lakes!” The city serves as the shortest crossing point between the east and west sides of the chain. Given this location, it is a hot spot for commuters, with over 17,000 vehicles passing through the east entrance every single day.


A Look at Windermere’s Past

Like much of the Sunshine State, Windermere was populated by indigenous people for tens of thousands of years. In the 16th century, it was home to the Timucuan Indians, who ruled the land until Spanish conquistadors began arriving in the mid 1500s.


The city was officially founded in 1925. It was named by early resident Dr. Stanley Scott. His father bought 160 acres and relocated to Windermere in 1885, building his homestead on the shores of Lake Butler. It is widely believed that Dr. Scott named the town after Lake Windermere, a beautiful lake in England.


Like much of Central Florida, citrus was a booming industry until harsh winters destroyed the crops. In order to ship the fruit across the country, Windermere was home to a railroad station. The Florida Midland Railroad, which is part of the Atlantic Coast Line Railroad, used to run just west of Main Street. Now, there is a large grassy area between Main Street and Dirt Main Street, which ran just west of the railroad.


Present-Day Windermere

What began as a place for wealthy northerners to “winter” slowly evolved into the American dream of retiring in Florida. Thanks to boating and lakefront living, locals enjoy an outdoors-focused way of life. Plus, the lakes offer never-ending stretches of waterfront real estate, helping the area boost enviable lots and high house prices.


Residents rave about the warm and friendly town, which is ranked as the ninth best suburb in the Orlando area. They appreciate everything from the variety of shops and restaurants to the winding roads and “abundance of cows.” It has a lovely downtown area and bustling main street. Town Square Park is another popular spot, thanks to weekly Farmers Market (pets welcome!), monthly Food Truck Night, and other local events.


The community is also within the highly-rated school system of Orange County and includes Windermere Elementary School, Gotha Middle School, and Olympia High School. Additionally, Windermere Preparatory School, a private, co-educational school that serves pre-K through 12th grade, is nearby in Lake Butler.



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