Luxury Real Estate in Windermere

Dating from the late 19th century, you’ll find contemporary elegance and the charm of a historic small town in Windermere. In addition, you’ll enjoy a selection of the area’s finest luxury communities, many of which focus on country club living and world-class golf and recreational amenities, attracting a host of celebrities and high-net worth individuals to this exclusive area. In-town convenience and walkability or the privacy of a gated enclave — the choice is yours in Windermere.

Life in Historic Windermere

Windermere is long on charm and offers many glimpses of its historic past. Many area homes in the historic downtown district are located on sandy, unpaved roads facing Lake Down, Lake Bessie, or Lake Butler. On Fridays, the town holds a well-known and well-attended weekly farmer’s market, bringing in folks from all over the area for local crafts, prepared foods, and produce stands.

You’ll also experience some of the area’s most unique dining and shopping, with local coffee and wine emporiums, cafes, and other retail options. For more extensive shopping excursions, you’re just minutes from some of Orlando’s best luxury shopping, including The Grove, Mall of Millennia, and Disney Springs.

Windermere Communities

You’ll find some of Orlando’s most exclusive gated communities in Windermere, including Isleworth and Lake Butler Sound. In addition, Keenes Pointe, Waterstone, Bellaria, Chaine du Lac, and a host of other neighborhoods are ensconced in this illustrious area. Bordering Doctor Philips and Winter Garden, Windermere offers close proximity to the many amenities and attractions of each of those neighborhoods, as well.

Windermere is known, in part, for the eclectic home styles you’ll find here, and offers a host of opportunities to indulge your personal architectural aesthetic. Students living in Windermere have the choice of highly-rated Orange County public schools as well as a number of well-regarded private schools, including Windermere Preparatory School in nearby Lake Butler. 

Find Your Home in Windermere

If you are interested in a luxury home in Windermere, Florida, Courtney Bass + Co. is waiting to help you narrow your search and find the home that truly offers everything you and your family are looking for. Here you’ll have the option of an historic in-town home with easy access to charming downtown shops and greenspaces or a lakeside estate home. Either way, your luxury real estate search will be focused on your unique preferences. Contact us to set up your custom search or begin your search here with this selection of the latest Windermere listings.

You may also SEARCH the MLS

New Listing - 4 weeks online
$1,675,000
Single Family Home For Sale
Active
4
BEDS
3
TOTAL BATHS
3,563
SQFT
1230 Kelso Boulevard
Windermere, FL 34786
Kelso On Lake Butler Subdivision
$2,650,000
Single Family Home For Sale
Active
4
BEDS
6
TOTAL BATHS
4,447
SQFT
11502 Waterstone Loop Drive
Windermere, FL 34786
Waterstone A D E F G H J L Subdivision
$2,895,000
Single Family Home For Sale
Active
4
BEDS
5
TOTAL BATHS
5,435
SQFT
11423 Waterstone Loop
Windermere, FL 34786
Waterstone Subdivision
Price Change - 2 weeks ago
$6,450,000
Single Family Home For Sale
Active
5
BEDS
8
TOTAL BATHS
10,112
SQFT
11049 Bridge House Road
Windermere, FL 34786
Reserve At Lake Butler Sound 45 120 Subdivision
New Listing - 2 weeks online
$7,775,000
Single Family Home For Sale
Active
6
BEDS
10
TOTAL BATHS
11,100
SQFT
9832 Laurel Valley Drive
Windermere, FL 34786
Isleworth Subdivision
Open House Fri, Aug 12, 3 PM UTC
$1,659,000
Single Family Home For Sale
Active
5
BEDS
5
TOTAL BATHS
5,229
SQFT
11737 Waterstone Loop Drive
Windermere, FL 34786
Waterstone Subdivision
$3,595,000
Single Family Home For Sale
Active
6
BEDS
8
TOTAL BATHS
9,046
SQFT
11000 Bridge House Road
Windermere, FL 34786
Reserve At Lake Butler Sound Subdivision
$3,650,000
Single Family Home For Sale
Active
5
BEDS
6
TOTAL BATHS
5,781
SQFT
5518 Worsham Court
Windermere, FL 34786
Isleworth 1st Amd Subdivision

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