Windermere Vacation Homes for Sale

Orlando vacation home buyers who appreciate luxury living, an abundance of water activities, and close proximity to area theme parks often find themselves choosing property in Windermere. The southwest Orange County town is just minutes from Walt Disney World and features some of the most affluent waterfront real estate in Central Florida.

Windermere is known as the “Town Among the Lakes” because it is located on an isthmus between several lakes in the Lake Butler chain of lakes. These beautiful lakes provide much of the appeal to full and part-time residents, who enjoy a variety of activities such as championship fishing, lake cruises, boating, canoeing and kayaking.


Check out the available Windermere vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the city!


Search Windermere Real Estate Listings

9927 GIFFIN CT,

9927 Giffin Ct, Windermere

1215310002
!!!! Nestled in one of Central Florida’s most exclusive 24-hour privately gate …more
$11,000,000
9718 CHESTNUT RIDGE DR,

9718 Chestnut Ridge Dr, Windermere

48110792
New Photos & Video Added! Poised on more than two acres along the shores of Lake …more
$7,120,000
5507 WORSHAM CT,

5507 Worsham Ct, Windermere

59102002
Custom estate perfectly situated on the 14th green of the Isleworth Country Club …more
$5,949,000
5318 ISLEWORTH COUNTRY CLUB DR,

5318 Isleworth Country Club Dr, Windermere

610122982
NEW PRICE! MOTIVATED SELLER OFFERS A $500,000. PRICE REDUCTION! WONDERFUL …more
$5,875,000
9905 LAKE LOUISE DR,

9905 Lake Louise Dr, Windermere

4771222
Nestled on more than an acre within the private guard-gated community of Islewor …more
$4,360,000
11307 BRIDGE HOUSE RD,

11307 Bridge House Rd, Windermere

5766612
Elegantly appointed Mediterranean home built by Ray Coudriet located on the Butl …more
$3,900,000
9713 ENDICOTT CT,

9713 Endicott Ct, Windermere

7878182
Nestled on a quiet cul-de-sac in Keene’s Pointe, this French country estate st …more
$3,900,000
6501 ROSELLA CT,

6501 Rosella Ct, Windermere

6980282
Beautifully sited on one acre on Lake Tibet Butler and located in prestigious gu …more
$3,895,000
9921 LAKE LOUISE DR,

9921 Lake Louise Dr, Windermere

5769652
Nestled on over an acre within the famed Isleworth Golf & Country Club, this sop …more
$3,800,000
9425 SKILES CT,

9425 Skiles Ct, Windermere

6779182
Keene’s Pointe, 24-hour gated/attended. This stunning golf front estate has mor …more
$3,799,000
6025 GREATWATER DR,

6025 Greatwater Dr, Windermere

7878122
MASTERFULLY CUSTOM DESIGNED BUTLER CHAIN OF LAKES ESTATE POSITIONED ON ONE OF TH …more
$3,650,000
11025 BRIDGE HOUSE RD,

11025 Bridge House Rd, Windermere

71095942
LAKE BUTLER. This stunning property embodies FLORIDA LIVING at its finest, with …more
$3,600,000

The Windermere Community

The town was chartered in 1925, but its history goes back much further, to 1889 when two Englishmen, the Rev. Joseph Hill Scott and his son Dr. Stanley Scott, started a settlement on the shores of Lake Butler. The town’s oldest structure is a one-room schoolhouse from that era, which has been restored to reflect its place as a site for educating children of citrus grove owners, workers and farm hands.

Today, Windermere features a quaint city center with charming shops and cafes, as well as a number of outstanding golf courses, such as The Golden Bear Club at Keene’s Pointe, designed by golfing great Jack Nicklaus and Isleworth, designed by golf legend Arnold Palmer.

Windermere Real Estate Market

In addition to waterfront luxury, Windermere also features stunning townhomes and condos that require less upkeep, while allowing you to relax in comfort and even enjoy the Disney fireworks from your backyard.


If you’d like more information about purchasing a second home in Windermere, contact a Team Donovan agent at 407.704.2616 or or visit us online.