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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!

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Active 9508 Windy Ridge Rd, WINDERMERE

$24,995,000

▼ $5,005,000 ACREAGE & UNREC

9508 Windy Ridge Rd, WINDERMERE

7 Beds 16 Baths 29,739 SqFt Single Family Residence MLS® # O6060999
Active 11301 Bridge House Rd, WINDERMERE

$11,995,000

RESERVE AT LAKE BUTLER SOUND

11301 Bridge House Rd, WINDERMERE

5 Beds 9 Baths 9,267 SqFt Single Family Residence MLS® # O6083126
Active 11035 Schooner Way, WINDERMERE

$8,250,000

▲ $750,000 MARINA BAY ESTATES

11035 Schooner Way, WINDERMERE

7 Beds 7 Baths 15,000 SqFt Single Family Residence MLS® # O5992601
Active 11940 Lake Butler Blvd, WINDERMERE

$8,250,000

▲ $1,255,000 METCALF PARK REP

11940 Lake Butler Blvd, WINDERMERE

5 Beds 7 Baths 6,549 SqFt Single Family Residence MLS® # O5992327
Active 5139 Isleworth Country Club Dr, WINDERMERE

$7,900,000

▼ $1,000,000 ISLEWORTH 01 AMD

5139 Isleworth Country Club Dr, WINDERMERE

7 Beds 8 Baths 13,973 SqFt Single Family Residence MLS® # O6026101
Active 9832 Laurel Valley Dr, WINDERMERE

$7,775,000

ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Single Family Residence MLS® # O6043474
Active 9520 Windy Ridge Rd, WINDERMERE

$7,500,000

ACREAGE & UNREC

9520 Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6069467
Active 10988 Down Yonder Ln, WINDERMERE

$7,500,000

LAKE DOWN ESTATES

10988 Down Yonder Ln, WINDERMERE

4 Beds 6 Baths 8,446 SqFt Single Family Residence MLS® # O6021133
Active 6507 Rosella Ct, WINDERMERE

$7,495,000

KEENES POINTE 46/104

6507 Rosella Ct, WINDERMERE

6 Beds 8 Baths 10,485 SqFt Single Family Residence MLS® # O6064654
Active 9736 Chestnut Ridge Dr, WINDERMERE

$7,388,000

ISLEWORTH

9736 Chestnut Ridge Dr, WINDERMERE

5 Beds 7 Baths 7,625 SqFt Single Family Residence MLS® # O6080321
Active 11947 Lake Butler Blvd, WINDERMERE

$7,035,000

LAKE BUTLER ESTATES

11947 Lake Butler Blvd, WINDERMERE

6 Beds 9 Baths 14,364 SqFt Single Family Residence MLS® # O6065698
Active 9838 Laurel Valley Dr, WINDERMERE

$7,000,000

ISLEWORTH

9838 Laurel Valley Dr, WINDERMERE

5 Beds 9 Baths 10,843 SqFt Single Family Residence MLS® # O6060724

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.

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