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Windermere Florida


‘Windermere among the lakes’—this beautiful, picturesque town is nestled among some of the most coveted real estate in all of Florida. Surrounded by an interconnected chain of 11 spring fed lakes, known as the Butler Chain. The downtown district features brick-paved streets throughout. This town combines modern luxury and sophistication with an “Old-Florida” feel.


Formed in 1915 and named for a city of the same name in England, Windermere has quietly become an enclave in which residents can escape the clamor of the nearby city and tourist attractions. Although a tiny town by Central Florida standards, Windermere boasts an impressive array of community activities and recreational pursuits. Located directly behind Walt Disney World and only about twenty minutes from downtown Orlando, Windermere living is as convenient as it is tranquil. Local highways are close but not so close as to intrude upon the serenity of the town and the surrounding area.

Education / Recreation

Windermere is home to three top-rated elementary schools, Windermere Elementary School, Keene’s Crossing Elementary School and Sunset Park Elementary School as well as Gotha Middle School, Bridgewater Middle School, Sunridge Middle School and Chain of Lakes Middle School. High Schools in the area include Olympia High School and West Orange High School. Another education option is the prestigious Windermere Preparatory School or Windermere Prep as the locals call it. A private, K-12 college preparatory school situated on the outskirts of downtown Windermere. Windermere Prep was voted best private school (K-8) in 2015 and hosts children from as many as 57 countries as they prepare for the next chapters in their lives.
When it comes to recreational water activities, Windermere rivals any coastal town. With seventy miles of shoreline, there are plenty of public and private boat ramps from which one can launch boats, jet skis, peddle boards, or whatever type of water craft that they their family and friends may enjoy. Pocket Lake, Lake Louise, Lake Butler and Lake Down, to name a few of the stunning waterways, provide endless opportunities for relaxation and exhilaration in the beautiful Florida sun. Additionally, the town hosts many events throughout the year to promote the community and enhance its resident’s enjoyment. Annual events like the Windermere Wine and Dine and the 5K Among the Lakes, among others, offer something for every taste and interest.

Economic / Shopping / Dining

The area is just minutes away from most of the area’s main attractions including the Mall at Millenia and the Disney Springs area, both of which feature high-end restaurants and retailers such as Apple, Macy’s, Neiman Marcus and many more. Additionally, downtown Windermere also offers a variety of services such as salons and professional offices all of which are designed in a way that is in sync with the architecture of the community and do not lend a commercial feel to the atmosphere of the beautiful downtown streets.

Real Estate

The real estate opportunities in Windermere offer something for everyone. From cozy, Florida-style single-family homes to lakefront estates in some of the area’s premier communities, there’s something to suit every taste and bank account. The centerpiece of the community is the gated community of Isleworth.
Featuring estate lakefront and golf course homes, Isleworth is one of the jewels of Southwest Orlando real estate. Stunning homes are interwoven into a natural landscape which has been designated an Audubon Cooperative Sanctuary. The exclusive Isleworth County Club provides a gorgeous option for recreation and dining close to home and helps to host the Tavistock Cup golf tournament every few years. There are plenty of great communities in the Windermere area such as, Keene’s Point—A Golden Bear Community, Belmere, Lake Butler Sound, and Harbor Isle, among many, many others. Many of communities throughout the town offer larger home sites and amenities which combine the luxury living experience with the small-town feel. With this many choices there are plenty of options for investors and resident-buyers alike. With strong property values and development, as well as its great location, Windermere is a perfect place to work, play, and buy a future home or investment property.



Keene’s Point

Lake Butler Sound

Harbor Isle

Anyone looking to make this town their next home can count on Julian Properties for assistance. Contact us today to start looking at Windermere, Florida real estate.