A charming, luxury town with easy access to the Butler Chain of Lakes and Orlando                         
Windermere is a small town southwest of Orlando, Florida. This charming, quaint town has a historic feel that dates back to its origins as a citrus farming mecca. Windermere’s historic buildings and rural feel have been preserved over the years, resulting in a luxury town with lots of classic Florida appeal. Windermere is located on the Butler Chain of Lakes and residents enjoy easy access to lake life, with jet skiing, boating, swimming, and more. The homes in the Windermere area are luxurious, built in a Mediterranean style with ample space both inside and out, and beautiful, meticulous landscaping. Many home developments feature guard-gated security for an added sense of privacy. This small town has high-class luxury living accommodations and offers the best of relaxing lake life near Orlando.
Residents in Windermere enjoy a small town, rural atmosphere, and access to the beautiful Butler Chain of Lakes. Lake life is key here and many stunning properties feature direct lake access. Residents also enjoy easy access to all that Orlando has to offer, with a vibrant nightlife scene and world-class theme parks.

What to Love

  • Luxury, lakefront properties, and sunshine all year round
  • Historic, small-town vibe
  • Easy access to Orlando
  • Seclusion, privacy, and gated home communities

Local Lifestyle

The lifestyle of Windermere is rich, luxurious, and rooted in small-town life. Residents enjoy an abundance of outdoor activities along the local lake system and plenty of privacy and seclusion. Windermere has some of the highest-rated schools, with lots of private and public options for families.

Dining, Entertainment & Shopping

Just outside Windermere is the Vinyard Wine Bar and Healthy Bistro. This stylish restaurant offers an elegant ambiance featuring private dining tables, an extensive wine menu, and a wine club. The menu includes creative favorites of both land and sea and fresh, local ingredients. The Agave Azul Cantina in Windermere serves Mexican classics in a festive, yet elegant setting with unique decor. Featuring friendly, high-class service and tasty Mexican favorites, the Agave Azul Cantina has something for the whole family. 
Black Rock Steakhouse offers a unique, interactive cooking experience, serving delicious Angus beef steaks on sizzling volcanic rock, cooked tableside. Nearby in Orlando, Fleming’s Prime Steakhouse and Winebar grills steaks to perfection in a more traditional setting and offers high-class, rich ambiance in a beautiful dining room, with options for catering and hosting large-scale events.

Things to Do

Isleworth Golf and Country Club is an exclusive, private golf community located on 600 acres along the Butler Lakes. Rich with high-class amenities and a private estate community, Isleworth offers award-winning golf in a picturesque setting along the Butler Lakes. Nearby, the Golden Bear Club boasts a perfectly manicured, 18-hole golf course designed by Jack Nicklaus, featuring luxury amenities in a world-class clubhouse. This full-service golf course offers tournaments, fundraising options, and corporate events in addition to private memberships.
Universal Orlando Resort is located nearby Windermere and offers something for the whole family. This world-class theme park offers immersive experiences, heart-stopping thrill rides, delicious food, an extensive water park, and more. Similarly, the Walt Disney World Resort is only a short drive from Windermere and is one of the best theme parks in the world. Immerse yourself into the Disney fantasy with delicious, themed foods from your favorite movies, greetings with characters, exciting rides, and more.


Windermere is served by Orange Country Public Schools and offers some of the best educational opportunities in the country with both private and charter options.

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