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

Sold
9927 GIFFIN CT,

9927 Giffin Ct, Windermere

1215310002
!!!! Nestled in one of Central Florida’s most exclusive 24-hour privately gated golf communities, Isleworth, is a rare and unique sprawlin …more
$11,000,000
11035 SCHOONER WAY,

11035 Schooner Way, Windermere

77150002
Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineerin …more
$7,500,000
Sold
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 Bessie, this extraordinary custom estate offers a prime lak …more
$7,120,000
11940 LAKE BUTLER BLVD,

11940 Lake Butler Blvd, Windermere

5765492
UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300’ SEAWALL. This private, gated lakefront home is set on 2.4 acres in o …more
$6,995,000
Sold
5018 LATROBE DR,

5018 Latrobe Dr, Windermere

710123532
Gracious lakefront living at its finest, this exquisite French chateau offers a prime location along the shores of Lake Bessie within the re …more
$6,900,000
11049 BRIDGE HOUSE RD,

11049 Bridge House Rd, Windermere

59101122
Presenting a custom-crafted Mediterranean mansion secluded behind its own private gates, perched along the shores of Lake Butler, inside gua …more
$6,450,000
5507 WORSHAM CT,

5507 Worsham Ct, Windermere

59102002
Custom estate perfectly situated on the 14th green of the Isleworth Country Club. This Isleworth mansion features an exquisite transitional, …more
$5,949,000
Sold
6462 DEACON CIR,

6462 Deacon Cir, Windermere

5671782
Nestled within the main gate of Isleworth Golf & Country Club along the shores of Lake Chase, this exquisite lakefront estate has been fully …more
$5,900,000
Sold
5318 ISLEWORTH COUNTRY CLUB DR,

5318 Isleworth Country Club Dr, Windermere

610122982
NEW PRICE! MOTIVATED SELLER OFFERS A $500,000. PRICE REDUCTION! WONDERFUL OPPORTUNITY TO PURHASE IN EXCLUSIVE GATED GOLF AND COUNTRY C …more
$5,875,000
Sold
9838 LAUREL VALLEY DR,

9838 Laurel Valley Dr, Windermere

58108432
Capturing majestic sunset views of beautiful Lake Butler, this fabulous lakefront estate is perfectly set between Lake Butler’s shoreline …more
$5,300,000
9905 LAKE LOUISE DR,

9905 Lake Louise Dr, Windermere

4771222
Nestled on more than an acre within the private guard-gated community of Isleworth, this extraordinary custom golf-front estate offers exqui …more
$4,360,000
Sold
50 FOREST ST,

50 Forest St, Windermere

6673882
CHECK OUT THE CUSTOM VIDEO… www.50forest.site/mls Estates like this are rarely available. This is your chance to call one of the best loc …more
$4,000,000

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.