Windermere/Butler Homes for Sale

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The historic town of Windermere was established in 1889. In 2004, the census estimated the population at 1,958. Known for its dirt roads and quaint atmosphere, Windermere is one of a dying breed of towns that has maintained that unique small-town feel that visitors and locals alike find so endearing.

Located in the town of Windermere, the Butler Chain of lakes is considered one of Florida’s most sought-after areas of lakefront property. The chain encompasses eleven lakes (Lake Butler, Lake Tibet, Lake Down, Lake Sheen, Lake Louise, Lake Chase, Pocket Lake, Lake Blanche, Wauseon Bay, Lake Isleworth, and Little Fish Lake), which have been recognized for their high water quality and animal habitats as “Outstanding Florida Waters” by Florida’s Department of Environmental Regulation.

Shaq’s House and Famous Windermere Residents

The Butler Chain of lakes has gained notoriety in recent years through high-profile residents who call Windermere their home. Shaquille O’Neil, Ken Griffey, Jr., Tiger Woods, Wesley Snipes, Planet Hollywood CEO Robert Earl, and Mark O’Meara are among many of the celebrities who enjoy this area’s magnificent lakefront views from their back yards.

Windermere’s Growing Pains

The areas of the southwest corner of Orange County and adjacent Lake County have exploded in growth in recent years, and Windermere with its small town charm has found itself wrestling with increasingly difficult issues of growth management.

The map below does a nice job of explaining the crux of the issue – the close proximity of Lake Down, Lake Butler and Lake Bessie combined with the layout of Main Street (fed by Maguire Road out of the Ocoee area) and Conroy-Windermere Road (out of the Metrowest area) has created a situation where so much of the traffic heading to the newer communities on the southwest part of town funnels through downtown Windermere. Despite these issues of growth, most everyone we know in Windermere wouldn’t trade it for any other location. Soaring property values, the serenity of the natural settings, and the small town charm combine to create one of the State’s most desirable lakefront communities.

Lake Info

Recreationally, the Windermere lakes offer phenomenal outlets both for waterskiing and fishing. All but Little Fish Lake are greater than 50 acres in surface area, providing more than ample space for ski boats and WaveRunners. Clear water, deep ledges and abundant vegetation foster plentiful schools of largemouth bass and bluegill, providing lucrative fishing year-round.

Lake Acreages

Click the lake name for more detailed information on water quality, depth, characteristics and ecology:

Boat Ramps

Public access is available through two boat ramps:

  1. Free entry is on Lake Down right off of Conroy-Windermere Rd. There, you will find a single-lane paved ramp with neither a dock nor any parking.
  2. However, Lake Isleworth is accessible for $5/day or $150/year at the R.D. Keene Park and Boat Rampon 10900 Chase Road. There is a paved double-lane ramp at the R.D. Keene Park, where you will also find a playground and multiple soccer fields.

The R.D. Keene Park may be contacted by phone at (407) 876-6696.

View Butler Chain of Lakes in a larger map

Community / School Info

In terms of amenities, schools, shopping, and overall standard of living, the Windermere area is considered one of Central Florida’s most desirable places to live.

A combination of top-notch private and public schools in the southwest area of Orange County offers Windermere parents a lot of great schooling options. For more information about Windermere area schools, please click the links below.

To search current year school rankings and data from the Florida Department of Education, please visit: