Vibrant and charming, Windermere is a small city, but it boasts big-city excitement.

Welcome to Windermere

An ultra-luxurious town known for its beautiful homes and world-class golf courses nestled among the Butler Chain of Lakes.

Nestled on an isthmus among the 11-lake Butler Chain of Lakes, Windermere lives up to its town motto of life “among the lakes.” Divided into two main sections, incorporated and unincorporated, this exclusive and beautiful town is world-renowned for its incredible homes, lakeside beauty, luxurious amenities, championship golf courses, and picturesque downtown area. The incorporated area is much smaller and controlled by the City of Windermere, while the unincorporated part is larger and regulated by Orange County.

Those planning to live here will reside in the lap of luxury, ideally positioned near the region’s best attractions such as downtown Orlando and beloved theme parks like Universal Orlando and Walt Disney World. Vibrant and charming, Windermere is a small city, but it boasts big-city excitement. This dazzling and unique town is a spectacular place to live with a pleasant, quiet atmosphere and highly-coveted homes that range from luxurious lakefront manors to small, cozy condominiums.

What to Love

  • Beautiful and elegant homes, some of the most luxurious in the world.
  • An assortment of lush, manicured parks and a waterfront recreation center.
  • Bustling downtown with an eclectic mix of restaurants, boutiques, entertainment.

Local Lifestyle

Those seeking mega-million mansions and lakeside estates are in luck. Windermere attracts wealthy residents from across the globe to its luxury lakefront lifestyle, world-class golfing, and beautiful homes, many of which are tucked behind exclusive gated communities.

The town is also home to the distinguished and popular Isleworth Golf and Country Club, a lavish community stretching across 600 acres recognized for its world-class amenities, championship golf courses, and some of Windermere’s most exquisite real estate. Lake Butler Sound is another affluent part of the community, as is the neighborhood of Olde Windermere, where you’ll find a lot of new construction.

That said, there are some more affordable options available as the housing options here are quite varied, ranging significantly from affordable townhomes to multi-million dollar manors.

Dining, Shopping and Entertainment

Most of Windermere’s dining, shopping, and entertainment is located in the downtown area. Coffee shops, small businesses, restaurants, and all kinds of unique shops compose the area with a nice variety of older buildings, too. This region is also where most of the town’s events are held, including food truck rallies, 5K runs, and holiday events.

Some of the most popular dining establishments:

  • Dixie Cream Café: bright and airy café once featured on The Rachael Ray Show plating southern comfort food made from scratch, plus, they have an excellent espresso bar.
  • Feather and Quill: top sit-down restaurant and craft cocktail bar with a diverse menu that makes really excellent and creative cocktails.
  • Pizza 14: sip from an icy glass bottle of soda while dining on a slice of wood-fire takeout pizza at one of the best pizza joints in town.

Things to Do

There is always something going on in Windermere, including family-friendly fun and farmers’ markets. The town hosts one of Florida’s most beautiful and unique 5K Run/Walk and 10K Run Among the Lakes that run along a scenic course around the lakes.

Come fall, families flock to the Halloween Costume Parade and Hayride. In the spring, Windermere hosts PetFest, a fun event for the entire family that features “paw-some” vendors, pet activities, food trucks, live music, police K-9 demonstrations and more in Town Square Park. During the holiday season, Windermere hosts a special “snowfall” event and Light Up Windermere to get residents into the Christmas spirit.

There are also a wide variety of beautiful parks in town along with a waterfront recreation center that has state-of-the-art facilities and scenic views of the lake. Enjoy a scenic picnic or barbecue in the park, go for a walk, or play a game of frisbee golf on the green.


Windermere is served by the Orange County Public School District, which includes Windermere Elementary, Gotha Middle, and Olympia High. Those living in the unincorporated part of town are zoned for Windermere High. Private education opportunities include Windermere Preparatory School, a co-ed PK-12 college preparatory school in nearby Lake Butler.
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