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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

$30,000,000

ACREAGE & UNREC

9508 Windy Ridge Rd, WINDERMERE

7 Beds 16 Baths 29,739 SqFt Single Family Residence MLS® # U8207115
Active 9306 Blanche Cove Dr, WINDERMERE

$16,500,000

▼ $1,000,000 ISLEWORTH

9306 Blanche Cove Dr, WINDERMERE

5 Beds 8 Baths 14,856 SqFt Single Family Residence MLS® # O6097686
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 5200 Isleworth Country Club Dr, WINDERMERE

$8,975,000

ISLEWORTH

5200 Isleworth Country Club Dr, WINDERMERE

5 Beds 8 Baths 9,482 SqFt Single Family Residence MLS® # O6124594
Active 6432 Deacon Cir, WINDERMERE

$8,300,000

ISLEWORTH

6432 Deacon Cir, WINDERMERE

5 Beds 9 Baths 11,021 SqFt Single Family Residence MLS® # O6120407
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 6120 Kirkstone Ln, WINDERMERE

$7,900,000

▼ $590,000 RESERVE AT LAKE BUTLER SOUND

6120 Kirkstone Ln, WINDERMERE

6 Beds 8 Baths 6,972 SqFt Single Family Residence MLS® # O6131593
Active 10988 Down Park Ln, WINDERMERE

$7,440,000

LAKE DOWN ESTATES

10988 Down Park Ln, WINDERMERE

4 Beds 6 Baths 8,446 SqFt Single Family Residence MLS® # O6021133
Active 11019 Bridge House Road R, WINDERMERE

$7,250,000

RESERVE AT LAKE BUTLER SOUND

11019 Bridge House Road R, WINDERMERE

7 Beds 11 Baths 9,376 SqFt Single Family Residence MLS® # O6115064
Active 6125 Grosvenor Shore Dr, WINDERMERE

$7,150,000

▼ $250,000 KEENES POINTE

6125 Grosvenor Shore Dr, WINDERMERE

6 Beds 7 Baths 8,287 SqFt Single Family Residence MLS® # O6103885
Active 9520 Windy Ridge Rd, windermere, Fl Rd, WINDERMERE

$7,000,000

ACREAGE & UNREC

9520 Windy Ridge Rd, windermere, Fl Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # U8211301
Active 9139 Tibet Pointe Cir, WINDERMERE

$6,500,000

KEENES POINTE 46/104

9139 Tibet Pointe Cir, WINDERMERE

6 Beds 9 Baths 10,341 SqFt Single Family Residence MLS® # O6080288
Active 5518 Worsham Ct, WINDERMERE

$6,450,000

ISLEWORTH 01 AMD

5518 Worsham Ct, WINDERMERE

5 Beds 8 Baths 8,100 SqFt Single Family Residence MLS® # O6141598
Active 11205 Bridge House Rd, WINDERMERE

$6,300,000

▼ $1,600,000 RESERVE AT LAKE BUTLER SOUND 45/120

11205 Bridge House Rd, WINDERMERE

6 Beds 8 Baths 8,330 SqFt Single Family Residence MLS® # O6088503
New
Active 5174 Vardon Dr, WINDERMERE

$5,975,000

ISLEWORTH

5174 Vardon Dr, WINDERMERE

6 Beds 9 Baths 10,701 SqFt Single Family Residence MLS® # O6143716
Active 12632 Park Ave, WINDERMERE

$5,950,000

▼ $250,000 CHAINE DU LAC

12632 Park Ave, WINDERMERE

6 Beds 9 Baths 10,213 SqFt Single Family Residence MLS® # O6123105
Active 11217 Bridge House Rd, WINDERMERE

$5,800,000

RESERVE AT LAKE BUTLER SOUND 45/120

11217 Bridge House Rd, WINDERMERE

6 Beds 8 Baths 6,755 SqFt Single Family Residence MLS® # O6136367
Active 10908 Down Yonder Ln, WINDERMERE

$5,500,000

LAKE DOWN ESTATES

10908 Down Yonder Ln, WINDERMERE

6 Beds 7 Baths 5,305 SqFt Single Family Residence MLS® # O6102219
Active 12422 Park Ave, WINDERMERE

$5,450,000

▲ $500,000 CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O5967251
Active 12300 Montalcino Cir, WINDERMERE

$4,949,990

▼ $5 CASA DEL LAGO REP

12300 Montalcino Cir, WINDERMERE

5 Beds 7 Baths 7,649 SqFt Single Family Residence MLS® # O6128915
Active 5084 Isleworth Country Club Dr, WINDERMERE

$4,750,000

ISLEWORTH

5084 Isleworth Country Club Dr, WINDERMERE

6 Beds 8 Baths 7,159 SqFt Single Family Residence MLS® # O6140732
Active 800 West 2nd Ave, WINDERMERE

$4,600,000

ALADAR ON LAKE BUTLER

800 West 2nd Ave, WINDERMERE

5 Beds 5 Baths 5,111 SqFt Single Family Residence MLS® # O6141389
Active 225 Magnolia St, WINDERMERE

$4,500,000

WINDERMERE TOWN

225 Magnolia St, WINDERMERE

7 Beds 11 Baths 5,735 SqFt Single Family Residence MLS® # O6079340
Active 4047 Isabella Cir, WINDERMERE

$4,380,000

CASABELLA PH 2

4047 Isabella Cir, WINDERMERE

5 Beds 8 Baths 8,372 SqFt Single Family Residence MLS® # O6118024
Active 9725 Chestnut Ridge Dr, WINDERMERE

$4,249,000

ISLEWORTH

9725 Chestnut Ridge Dr, WINDERMERE

5 Beds 6 Baths 6,885 SqFt Single Family Residence MLS® # O6128678
Active 801 West 2nd Ave, WINDERMERE

$3,995,000

ALADAR ON LAKE BUTLER

801 West 2nd Ave, WINDERMERE

5 Beds 6 Baths 5,639 SqFt Single Family Residence MLS® # O6093610
Active 7545 Ficquette Rd, WINDERMERE

$3,950,000

7545 Ficquette Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # S5074124
Active 5373 Isleworth Country Club Dr, WINDERMERE

$3,900,000

ISLEWORTH

5373 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 5,372 SqFt Single Family Residence MLS® # O6140129
Active 9950 6th St, WINDERMERE

$3,499,900

GOTHA

9950 6th St, WINDERMERE

4 Beds 6 Baths 5,526 SqFt Single Family Residence MLS® # O6125748
Active 4071 Isabella Cir, WINDERMERE

$3,490,000

CASABELLA PH 2

4071 Isabella Cir, WINDERMERE

5 Beds 8 Baths 6,752 SqFt Single Family Residence MLS® # O6121777
Active 11118 Coniston Way, WINDERMERE

$3,395,000

RESERVE AT LAKE BUTLER SOUND UNIT 02

11118 Coniston Way, WINDERMERE

5 Beds 7 Baths 8,128 SqFt Single Family Residence MLS® # O6131361
Active 325 Magnolia St, WINDERMERE

$2,998,000

WINDERMERE TOWN

325 Magnolia St, WINDERMERE

4 Beds 3 Baths 3,975 SqFt Single Family Residence MLS® # O6133619
New
Active 5054 Sawyer Cove Way, WINDERMERE

$2,900,000

SAWYER SOUND

5054 Sawyer Cove Way, WINDERMERE

5 Beds 7 Baths 5,353 SqFt Single Family Residence MLS® # O6139313
Active 12624 Park Ave, WINDERMERE

$2,895,000

CHAINE DU LAC

12624 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6137328
Active 803 West 2nd Ave, WINDERMERE

$2,750,000

▼ $50,000 ALADAR ON LAKE BUTLER

803 West 2nd Ave, WINDERMERE

4 Beds 4 Baths 2,819 SqFt Single Family Residence MLS® # O6129915
Active 803 West 2nd Ave, WINDERMERE

$2,750,000

▼ $50,000 ALADAR ON LAKE BUTLER

803 West 2nd Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6130226
Active 10988 Down Park Ln, WINDERMERE

$2,500,000

▼ $200,000 LAKE DOWN ESTATES

10988 Down Park Ln, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6064399
Active 10908 Down Yonder Ln, WINDERMERE

$2,500,000

▲ $75,000 LAKE DOWN ESTATES

10908 Down Yonder Ln, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6060381
Active 1238 Lake Whitney Dr, WINDERMERE

$2,475,000

▼ $25,000 RESERVE AT BELMERE PH 02 48 144

1238 Lake Whitney Dr, WINDERMERE

4 Beds 6 Baths 5,514 SqFt Single Family Residence MLS® # L4933072
Active 1003 Oakdale St, WINDERMERE

$2,300,000

▼ $350,000 WINDERMERE TOWN

1003 Oakdale St, WINDERMERE

5 Beds 5 Baths 4,061 SqFt Single Family Residence MLS® # O6116062
Active 9907 Beaufort Ct, WINDERMERE

$2,199,900

KEENES POINTE

9907 Beaufort Ct, WINDERMERE

4 Beds 4 Baths 4,658 SqFt Single Family Residence MLS® # O6136847
New
Active 1220 Lake Whitney Dr, WINDERMERE

$2,199,000

RESERVE AT BELMERE PH 02 48 144

1220 Lake Whitney Dr, WINDERMERE

6 Beds 7 Baths 6,184 SqFt Single Family Residence MLS® # O6144874
Active 81 Oakdale St, WINDERMERE

$2,199,000

▼ $90,000 DAVIS SHORES

81 Oakdale St, WINDERMERE

5 Beds 5 Baths 4,284 SqFt Single Family Residence MLS® # O6116858
Active 9012 Pinnacle Cir, WINDERMERE

$1,975,000

▼ $75,000 LAKE DOWN CREST

9012 Pinnacle Cir, WINDERMERE

4 Beds 5 Baths 3,585 SqFt Single Family Residence MLS® # O6129290
Active 8248 Tibet Butler Dr, WINDERMERE

$1,949,000

▼ $50,000 KEENES POINTE

8248 Tibet Butler Dr, WINDERMERE

5 Beds 4 Baths 4,706 SqFt Single Family Residence MLS® # O6123335
Active 2508 Hempel Cove Ct, WINDERMERE

$1,890,000

▼ $60,000 LAKE DOWN COVE

2508 Hempel Cove Ct, WINDERMERE

5 Beds 6 Baths 5,478 SqFt Single Family Residence MLS® # O6125618
Active 311 East 8th Ave, WINDERMERE

$1,850,000

WINDERMERE TOWN

311 East 8th Ave, WINDERMERE

5 Beds 4 Baths 3,805 SqFt Single Family Residence MLS® # O6141867
Active 520 Haley Dr, WINDERMERE

$1,785,000

▼ $165,000 CRESCENT LAKE ESTATES

520 Haley Dr, WINDERMERE

4 Beds 4 Baths 4,283 SqFt Single Family Residence MLS® # O6129388

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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