Learn What Makes Windermere a Wonderful Community to Live In


Windermere is a small town located in Southwest Orlando. It is known to be a town located among the lakes. Windermere is located on the Butler chain of Lakes. The Butler chain of Lakes consist of eleven connected natural lakes. Each lake having its own charm, but not all are skiable. The larger lakes are known for fishing and skiing.

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Holiday Events


The quant small town living comes alive on Friday mornings when the community has their farmers market, and on one Friday night, typically the third Friday of the month, with Food Truck night. Local Food Trucks park along the downtown area. Families come out with their tables and chairs, as well as their family to enjoy the food and each others company. Particularly great during the fall and early spring with cooler nights. The kids bring basketballs and play of the courts. Sometimes there are movie nights for the kids as well. Other times, there is live music playing. The community is a family friend town having family events such as a community trick or treating event on Halloween, Lighting up the trees and decorating for Christmas, and various other celebrations throughout the years. It is a town that has managed to keep some of it’s small town charm.


The schools of Windermere are among the best in Central Florida. One of the most prestigious is Windermere Prep. Windermere Prep is a private school focusing on high academic achievement. Among the other local schools such as Windermere, Sunset Park and Keene’s Crossing Elementary Schools are all “A” rated schools and very well-regarded. The current public elementary schools for Windermere Florida is Keene’s CrossingWindermereSunset Park, and Lake Whitney. The list of public middle schools are BridgewaterGotha, and Chain of Lakes.

There are two public high schools at this time Olympia and West Orange. In addition to these schools, the community is awaiting a new high school which will be located on a 65-acre property is along County Road 535 (Winter Garden-Vineland Road) at the northeast corner of an intersection that includes 535 to the north and east, Summerport Village Parkway to the west and Ficquette Hancock Road to the south. School zones change so be sure to verify the school by address before purchasing a property with Orange County Public Schools. The school grades also change. It is a good idea to look at grades over a few year period to get an idea on the overall character of a school.


With lakes on all boarders of the community, this small town has managed to keep its small charm by keeping many of its street unpaved as well as strictly enforcing a low-speed limit. The town has also installed several roundabouts to restrict speed. There are several signs posted stating that speed is strictly enforced, and the police do strictly enforce the speed as well as ticketing to those attempting to cut through the town on the side or non-paved roads. Some have mentioned tickets for just a few miles over the speed limit. The town has implemented these options due to the high number of commuters cutting through the town, many of which come from Winter Garden.
Winter Garden lies to the west of Windermere; and Dr Phillips lies to the east of Windermere. It is a fast growing area with lots of new home builders. Homeowners looking for good schools and new homes have ventured into the Windermere and Winter Garden area which has now exploded with development. Some of the congestion and traffic in the downtown area have been cut down with the construction and completion of the Winter Garden Village which is an outdoor shopping area with lots of restaurants. Previously, residents in the Winter Garden area would cut through Windermere to get to the Dr Phillips area in search of restaurants as well as the shopping at some of the malls not far away from the Dr Phillips area.

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The major lakes which make Windermere “among the lakes” are known for boating and fishing. There are 11 lakes that comprise the Butler Chain. The lakes are in varying sizes. Some are not large enough for skiing while others are. Boating is a big hobby. Bass fishing is also very popular. Homes located on these lakes have high price tags. Homes with docks have larger price tags. And, homes on the largest lake, Lake Butler, with boat docks have very large price tags. Lake Butler dock homes are among the most luxurious in Orlando.


Home prices in Windermere are typically on the higher end. There are many luxury homes. Vacant lots along the shores of Lake Butler have been known to sell over a million. Newer and renovated homes on Lake Butler with boat docks are highly sought after and have a large price tag. One of the most prestigious communities in Windermere is Isleworth home to several famous individuals. Various gated and guard gated communities are located within Windermere with such famous residents as Grant Hill, Pedro Feliz, Arnold Palmer, Robert Earl, Ken Griffey Jr., Stuart Appleby, Wesley Snipes and Shaq.
If you are looking to find your own piece of this wonderful community, please let us know.If you are looking for homes in the Windermere area, please take a look at all the homes currently on the market in the MLS in Windermere. We can help you with finding the home of your dreams.