Residents enjoy the quietude of neighborhood streets and relishing their seclusion.

Welcome to Windermere

A peaceful oasis just outside of Orlando

Windermere is a town in Orange County, Florida, with over 3,000 residents within the Orlando Metropolitan Area, providing residents a quintessentially Floridian experience. The town was established as a residential area in 1889 and chartered in 1925, making it one of the oldest communities in Orange County.
This community has a small footprint, measuring less than two square miles, and residents enjoy the quietude of neighborhood streets, relishing their seclusion from the city’s nearby hustle and bustle. One of its most notable developments is Isleworth, a famous golf course, gated community with an air of prestige and privacy.

What to Love

  • A quiet oasis hideaway near Orlando, tucked between Lakes Butler, Down, and Bessie
  • Peaceful residential streets with easy access to the greater metropolitan area
  • ​​​​​​​Close-knit community without the traffic or noise of the city

Local Lifestyle

Windermere's local lifestyle is one of seclusion, and it's preferred that way. Because the area features such high-end clientele, great food and wine choices are never far. You’ll enjoy taking advantage of Orlando’s nearby amenities while being able to relax in the privacy of your Windermere estate.

Dining, Entertainment & Shopping

Tim's Wine Market is an excellent stop for many who want to partake in one (or several) of the over 700 selections of wine that Tim's has to offer. Next door to Tim's is the Dixie Cream Cafe, a popular spot for breakfast or lunch. The Cafe has been featured on the Rachel Ray Show. A short drive away — of course, in a town that's only 1.57 square miles, everything is a short drive away — you can also enjoy lunch at Yellow Dog East Cafe.

Things to Do

Spanning 600 acres among Central Florida's Butler Chain of Lakes is Isleworth. Not only is this community the home of Tiger Woods, but it's also considered one of the most prestigious private golf clubs in the world and features championship golf, amenities, and luxury estate homes across the property.

The Florida Ski School, owned and operated by Franck Desboyaux (currently ranked 2nd in the world in competitive skiing), offers an opportunity to experience the joys of water skiing, wake surfing, or wakeboarding. Franck and his staff offer lessons for adults and children, or you can also book a sunset cocktail cruise for up to 13 people. 

If you're looking for something less active and more on the relaxing side of life, check out the Indigo Spa & Wellness Center. It promises a different approach to the spa experience and brings you the best customer service for ultimate relaxation.


The public school district serving Windermere is the Orange School District, catering to over 200,000 students across 263 schools, grades PK-12.

  • Windermere Elementary, PK-5
  • Windermere High, 9-12
  • Windermere Preparatory School, PK-12
  • Olympia High, 9-12 
  • Sunset Park Elementary, K-5
  • Cornerstone Academy Charter, K-8
  • Cornerstone Academy Charter High, 9-12

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