Windermere, Florida is an affluent suburb in Southwest Orlando, Florida. The area is well known for its beautiful trees and being nestled among the gorgeous Butler Chain of Lakes. “Among the Lakes” is the phrase commonly associated with the town of Windermere.


Despite being a very small geographic footprint in Orlando, Windermere is very well known due to the Butler Chain of Lakes as well as nearby famous neighborhoods such Isleworth which are home to famous athletes such as Shaquille O’Neal, Tiger Woods, and more.


The restaurants in downtown Windermere are somewhat limited as there are only a few commercial properties. However, Dixie Cream Cafe has become somewhat popular, especially for breakfast and lunch crowds. Dixie Cream Cafe is located in the space that was occupied for years by the Ready Market. Allen’s is a local ice cream shop that also serves coffee, donuts and yes, BBQ.

Many Windermere residents travel the short distance to other restaurants either in Dr. Phillips (restaurant row) or up Maguire to the Ocoee / Winter Garden areas.

Family & Fitness

Easily one of the most popular family activities for Windermere residents is boating on the Butler Chain of Lakes. There are a couple public boat drop-ins located on Conroy Rd. and another nearby Keenes Point if you don’t have private access.

LA Fitness is a great facility located at the intersection of Apopka Vineland and Conroy Rd. Also, residents on the northern side of Windermere may find the Roper YMCA a good option.

Windermere Little League is a popular sports league for youngsters with facilities adjacent to Windermere Elementary School as well as adjacent to George Bailey Park off Roberson Rd.

On Friday mornings, there is a small farmer’s market in downtown Windermere.


Windermere Elementary School, Gotha Middle School, Olympia High School

Windermere Prep is a private school located in the area.