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WINDERMERE VACATION HOMES FOR SALE

City:  Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion |  Windermere | Winter Garden

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 5603 Marleon Dr, WINDERMERE

$27,000,000

NA

5603 Marleon Dr, WINDERMERE

7 Beds 10 Baths 22,108 SqFt Residential Single Family Residence MLS® # O6404938
Active 5192 Vardon Dr, WINDERMERE

$19,500,000

ISLEWORTH AMD 03

5192 Vardon Dr, WINDERMERE

6 Beds 10 Baths 13,494 SqFt Residential Single Family Residence MLS® # O6441344
Active 5036 Latrobe Dr, WINDERMERE

$18,750,000

ISLEWORTH

5036 Latrobe Dr, WINDERMERE

6 Beds 9 Baths 15,337 SqFt Residential Single Family Residence MLS® # O6441249
Active 6119 Grosvenor Shore Dr, WINDERMERE

$15,900,000

KEENES POINT

6119 Grosvenor Shore Dr, WINDERMERE

8 Beds 11 Baths 14,068 SqFt Residential Single Family Residence MLS® # O6421205
Active 12488 Park Ave, WINDERMERE

$15,500,000

CHAINE DU LAC

12488 Park Ave, WINDERMERE

10 Beds 17 Baths 13,425 SqFt Residential Single Family Residence MLS® # O6395291
Active 3057 Porto Lago Ct, WINDERMERE

$13,995,000

LAKE DOWN POINTE 50 42

3057 Porto Lago Ct, WINDERMERE

6 Beds 11 Baths 12,067 SqFt Residential Single Family Residence MLS® # O6411245
Active 9323 Gladys Garden Ct, WINDERMERE

$11,900,000

▼ $600,000 ISLEWORTH

9323 Gladys Garden Ct, WINDERMERE

6 Beds 10 Baths 9,770 SqFt Residential Single Family Residence MLS® # O6381880
Active 9832 Laurel Valley Dr, WINDERMERE

$11,750,000

▼ $1,000,000 ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Residential Single Family Residence MLS® # O6416194
Active 4226 Downeast Ln, WINDERMERE

$9,750,000

▼ $750,000

4226 Downeast Ln, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6367852
Active 4226 Downeast Ln, WINDERMERE

$9,750,000

▼ $750,000 NA

4226 Downeast Ln, WINDERMERE

5 Beds 3 Baths 5,316 SqFt Residential Single Family Residence MLS® # O6355233
Active 12422 Park Ave, WINDERMERE

$8,695,000

CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6416090
New
Active 5092 Isleworth Country Club Dr, WINDERMERE

$8,500,000

ISLEWORTH

5092 Isleworth Country Club Dr, WINDERMERE

4 Beds 5 Baths 7,100 SqFt Residential Single Family Residence MLS® # O6446272
Active 9343 Tibet Pointe Cir, WINDERMERE

$7,450,000

KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Residential Single Family Residence MLS® # O6443379
Active 5074 Isleworth Country Club Dr, WINDERMERE

$7,250,000

▼ $345,000 ISLEWORTH

5074 Isleworth Country Club Dr, WINDERMERE

5 Beds 7 Baths 7,099 SqFt Residential Single Family Residence MLS® # O6373191
Active 5373 Isleworth Country Club Dr, WINDERMERE

$7,200,000

ISLEWORTH

5373 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 5,993 SqFt Residential Single Family Residence MLS® # O6439156
Active 9349 Tibet Pointe Cir, WINDERMERE

$6,995,000

▼ $405,000 KEENES POINTE

9349 Tibet Pointe Cir, WINDERMERE

5 Beds 8 Baths 7,529 SqFt Residential Single Family Residence MLS® # O6404415
New
Active 6113 Grosvenor Shore Dr, WINDERMERE

$6,950,000

KEENES POINTE

6113 Grosvenor Shore Dr, WINDERMERE

7 Beds 8 Baths 8,722 SqFt Residential Single Family Residence MLS® # O6443311
Active 6055 Louise Cove Dr, WINDERMERE

$6,900,000

▼ $100,000 ISLEWORTH WEST

6055 Louise Cove Dr, WINDERMERE

5 Beds 6 Baths 7,158 SqFt Residential Single Family Residence MLS® # O6430931
Active 9061 Ron Den Ln, WINDERMERE

$6,800,000

▼ $100,000 DOWN ACRES ESTATES

9061 Ron Den Ln, WINDERMERE

5 Beds 7 Baths 6,300 SqFt Residential Single Family Residence MLS® # O6417446
Active 8342 Boyla Ct, WINDERMERE

$6,700,000

KEENES POINTE

8342 Boyla Ct, WINDERMERE

8 Beds 10 Baths 8,133 SqFt Residential Single Family Residence MLS® # O6422852
Active 9921 Lake Louise Dr, WINDERMERE

$6,650,000

ISLEWORTH

9921 Lake Louise Dr, WINDERMERE

5 Beds 7 Baths 6,970 SqFt Residential Single Family Residence MLS® # O6429164
Active 6462 Deacon Cir, WINDERMERE

$6,595,000

ISLEWORTH

6462 Deacon Cir, WINDERMERE

5 Beds 6 Baths 7,178 SqFt Residential Single Family Residence MLS® # O6407107
Active 9316 Gladys Garden Ct, WINDERMERE

$6,500,000

ISLEWORTH

9316 Gladys Garden Ct, WINDERMERE

5 Beds 7 Baths 5,471 SqFt Residential Single Family Residence MLS® # O6420326
Open House
Active 800 W 2nd Ave, WINDERMERE

$5,999,000

ALADAR ON LAKE BUTLER

800 W 2nd Ave, WINDERMERE

5 Beds 5 Baths 5,511 SqFt Residential
Sun, Oct 4th, 2026 @ 12pm - 2pm
Single Family Residence MLS® # O6422976
Active 9725 Chestnut Ridge Dr, WINDERMERE

$5,975,000

▼ $25,000 ISLEWORTH

9725 Chestnut Ridge Dr, WINDERMERE

7 Beds 7 Baths 8,000 SqFt Residential Single Family Residence MLS® # O6370294
Active 1330 Lake Olivia, WINDERMERE

$5,500,000

LAKE OLIVIA RESERVE

1330 Lake Olivia, WINDERMERE

6 Beds 8 Baths 6,442 SqFt Residential Single Family Residence MLS® # S5155388
Active 12264 Montalcino Cir, WINDERMERE

$5,390,000

CASA DEL LAGO REP

12264 Montalcino Cir, WINDERMERE

4 Beds 7 Baths 7,872 SqFt Residential Single Family Residence MLS® # O6404587
Active 5199 Latrobe Dr, WINDERMERE

$5,300,000

ISLEWORTH

5199 Latrobe Dr, WINDERMERE

6 Beds 7 Baths 4,665 SqFt Residential Single Family Residence MLS® # O6409961
Active Windy Ridge Rd, WINDERMERE

$5,250,000

▲ $750,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439497
Active 5138 Fairway Oaks Dr, WINDERMERE

$4,999,500

ISLEWORTH

5138 Fairway Oaks Dr, WINDERMERE

4 Beds 5 Baths 4,330 SqFt Residential Single Family Residence MLS® # O6401757
Active 5070 Down Point Ln, WINDERMERE

$4,995,000

SUNSET BAY

5070 Down Point Ln, WINDERMERE

6 Beds 7 Baths 7,349 SqFt Residential Single Family Residence MLS® # O6385276
Active 9721 Carillon Park Dr, WINDERMERE

$4,778,000

▼ $222,000 KEENES POINTE

9721 Carillon Park Dr, WINDERMERE

6 Beds 9 Baths 8,305 SqFt Residential Single Family Residence MLS® # O6336879
Active 9575 Westover Roberts Rd, WINDERMERE

$4,750,000

▼ $100,000 GOTHA TOWN

9575 Westover Roberts Rd, WINDERMERE

7 Beds 8 Baths 8,931 SqFt Residential Single Family Residence MLS® # O6357873
Active Windy Ridge Rd, WINDERMERE

$4,750,000

▲ $500,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439342
Active 6719 Valhalla Way, WINDERMERE

$4,495,000

KEENES POINTE 46/104

6719 Valhalla Way, WINDERMERE

5 Beds 7 Baths 6,159 SqFt Residential Single Family Residence MLS® # O6428554
Active 5186 Vardon Dr, WINDERMERE

$4,395,000

ISLEWORTH

5186 Vardon Dr, WINDERMERE

6 Beds 6 Baths 4,739 SqFt Residential Single Family Residence MLS® # O6443681
Active 12418 Park Ave, WINDERMERE

$4,395,000

CHAINE DU LAC

12418 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6370377
Active Windy Ridge Rd, WINDERMERE

$4,250,000

▼ $250,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439500
Active 9144 Isleworth Gardens Dr, WINDERMERE

$4,100,000

▼ $200,000 ISLEWORTH

9144 Isleworth Gardens Dr, WINDERMERE

3 Beds 5 Baths 5,004 SqFt Residential Single Family Residence MLS® # O6397842
New
Active 6120 Greatwater Dr, WINDERMERE

$3,999,000

KEENES POINTE

6120 Greatwater Dr, WINDERMERE

5 Beds 6 Baths 5,580 SqFt Residential Single Family Residence MLS® # O6445244
Active 4201 Isabella Cir, WINDERMERE

$3,990,000

▼ $10,000 CASABELLA

4201 Isabella Cir, WINDERMERE

6 Beds 7 Baths 6,896 SqFt Residential Single Family Residence MLS® # O6430081
Active 11002 Lake Butler Blvd, WINDERMERE

$3,950,000

▼ $49,999 METCALF PARK REP

11002 Lake Butler Blvd, WINDERMERE

5 Beds 8 Baths 6,248 SqFt Residential Single Family Residence MLS® # O6284922
New
Active 4906 Aviva Garden Ct, WINDERMERE

$3,850,000

ISLEWORTH

4906 Aviva Garden Ct, WINDERMERE

4 Beds 6 Baths 6,605 SqFt Residential Single Family Residence MLS® # O6446042
Active 5151 Latrobe Dr, WINDERMERE

$3,800,000

▼ $100,000 ISLEWORTH

5151 Latrobe Dr, WINDERMERE

4 Beds 5 Baths 5,301 SqFt Residential Single Family Residence MLS® # O6392380
Active 9960 6th St, WINDERMERE

$3,750,000

GOTHA TOWN

9960 6th St, WINDERMERE

5 Beds 6 Baths 6,182 SqFt Residential Single Family Residence MLS® # O6412077
Active 3986 Isabella Cir, WINDERMERE

$3,599,000

CASABELLA PH 2

3986 Isabella Cir, WINDERMERE

5 Beds 7 Baths 5,342 SqFt Residential Single Family Residence MLS® # O6432946
New
Active 9310 Isleworth Gardens Dr, WINDERMERE

$3,595,000

ISLEWORTH

9310 Isleworth Gardens Dr, WINDERMERE

3 Beds 5 Baths 4,333 SqFt Residential Single Family Residence MLS® # O6442366
Active 4302 Isabella Cir, WINDERMERE

$3,580,000

▼ $120,000 CASABELLA

4302 Isabella Cir, WINDERMERE

5 Beds 7 Baths 5,362 SqFt Residential Single Family Residence MLS® # O6436735

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.

Communities in Windermere, Florida


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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