WINDERMERE VACATION HOMES FOR SALE

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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

$8,475,000

▼ $500,000 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 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 6125 Grosvenor Shore Dr, WINDERMERE

$6,999,000

KEENES POINTE

6125 Grosvenor Shore Dr, WINDERMERE

6 Beds 7 Baths 8,037 SqFt Single Family Residence MLS® # O6151049
Active 6120 Kirkstone Ln, WINDERMERE

$6,890,000

▼ $1,010,000 RESERVE AT LAKE BUTLER SOUND

6120 Kirkstone Ln, WINDERMERE

6 Beds 8 Baths 6,972 SqFt Single Family Residence MLS® # O6131593
New
Active 5190 Latrobe Dr, WINDERMERE

$6,500,000

ISLE 4TH AMD

5190 Latrobe Dr, WINDERMERE

5 Beds 7 Baths 7,191 SqFt Single Family Residence MLS® # O6159303
Active 10821 Bayshore Dr, WINDERMERE

$6,490,000

BAYSHORE ESTATES

10821 Bayshore Dr, WINDERMERE

4 Beds 6 Baths 5,275 SqFt Single Family Residence MLS® # O6157691
New
Active 5226 Isleworth Country Club Dr, WINDERMERE

$5,995,000

ISLEWORTH

5226 Isleworth Country Club Dr, WINDERMERE

5 Beds 9 Baths 7,821 SqFt Single Family Residence MLS® # O6157478
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 10 Baths 10,213 SqFt Single Family Residence MLS® # O6123105
Active 12540 Park Ave, WINDERMERE

$5,800,000

CHAINE DE LAC

12540 Park Ave, WINDERMERE

5 Beds 7 Baths 7,736 SqFt Single Family Residence MLS® # O6151810
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 11217 Bridge House Rd, WINDERMERE

$5,350,000

▼ $250,000 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 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 225 Magnolia St, WINDERMERE

$4,500,000

WINDERMERE TOWN

225 Magnolia St, WINDERMERE

7 Beds 11 Baths 5,935 SqFt Single Family Residence MLS® # O6079340
Active 9247 Tibet Pointe Cir, WINDERMERE

$4,450,000

KEENES POINTE 46/104

9247 Tibet Pointe Cir, WINDERMERE

6 Beds 7 Baths 6,849 SqFt Single Family Residence MLS® # O6157160
Active 4807 Alexandra Garden Ct, WINDERMERE

$4,400,000

ISLEWORTH

4807 Alexandra Garden Ct, WINDERMERE

4 Beds 6 Baths 5,741 SqFt Single Family Residence MLS® # O6155478
Active 4047 Isabella Cir, WINDERMERE

$3,999,000

▲ $3,599,100 CASABELLA PH 2

4047 Isabella Cir, WINDERMERE

6 Beds 8 Baths 8,372 SqFt Single Family Residence MLS® # O6158850
Active 9725 Chestnut Ridge Dr, WINDERMERE

$3,995,000

▼ $254,000 ISLEWORTH

9725 Chestnut Ridge Dr, WINDERMERE

5 Beds 6 Baths 6,885 SqFt Single Family Residence MLS® # O6128678
Active 7545 Ficquette Rd, WINDERMERE

$3,950,000

7545 Ficquette Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # S5074124
Active 800 West 2nd Ave, WINDERMERE

$3,900,000

▼ $700,000 ALADAR ON LAKE BUTLER

800 West 2nd Ave, WINDERMERE

5 Beds 5 Baths 5,111 SqFt Single Family Residence MLS® # O6141389
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 7 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 5186 Vardon Dr, WINDERMERE

$3,095,000

ISLEWORTH

5186 Vardon Dr, WINDERMERE

4 Beds 5 Baths 4,739 SqFt Single Family Residence MLS® # O6157870
Active 2006 Bellamere Ct, WINDERMERE

$3,090,000

▼ $90,000 BELLA VITA ESTATES

2006 Bellamere Ct, WINDERMERE

5 Beds 5 Baths 5,043 SqFt Single Family Residence MLS® # O6152144
Active 9042 Pinnacle Cir, WINDERMERE

$2,995,000

▼ $155,000 LAKE DOWN CREST

9042 Pinnacle Cir, WINDERMERE

7 Beds 6 Baths 8,461 SqFt Single Family Residence MLS® # O6150530
Active 325 Magnolia St, WINDERMERE

$2,988,000

▼ $10,000 WINDERMERE TOWN

325 Magnolia St, WINDERMERE

4 Beds 3 Baths 3,975 SqFt Single Family Residence MLS® # O6133619
Active 2012 Bellamere Ct, WINDERMERE

$2,950,000

BELLA VITA ESTATES

2012 Bellamere Ct, WINDERMERE

5 Beds 6 Baths 4,688 SqFt Single Family Residence MLS® # O6145734
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 13334 Bellaria Cir, WINDERMERE

$2,699,000

BELLARIA

13334 Bellaria Cir, WINDERMERE

5 Beds 7 Baths 5,734 SqFt Single Family Residence MLS® # O6152745
Active 2455 Maguire Rd, WINDERMERE

$2,600,000

LAKE DOWN ESTATES

2455 Maguire Rd, WINDERMERE

4 Beds 5 Baths 3,987 SqFt Single Family Residence MLS® # O6158520
Active 1815 Windermere Rd, WINDERMERE

$2,499,000

NOT APPLICABLE

1815 Windermere Rd, WINDERMERE

4 Beds 5 Baths 4,290 SqFt Single Family Residence MLS® # O6148700
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 9204 Tibet Pointe Cir, WINDERMERE

$2,400,000

KEENES POINTE 46/104

9204 Tibet Pointe Cir, WINDERMERE

5 Beds 6 Baths 5,291 SqFt Single Family Residence MLS® # T3475778
New
Active 9025 Balmoral Mews Sq, WINDERMERE

$2,399,999

BALMORAL

9025 Balmoral Mews Sq, WINDERMERE

5 Beds 5 Baths 4,463 SqFt Single Family Residence MLS® # O6159129
Active 1128 Estancia Woods Loop, WINDERMERE

$2,349,000

▲ $49,000 ESTANCIA AT WINDERMERE

1128 Estancia Woods Loop, WINDERMERE

5 Beds 7 Baths 5,382 SqFt Single Family Residence MLS® # O6151628
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 2804 Midsummer Dr, WINDERMERE

$2,300,000

▼ $100,000 LAKE DOWN SHORES REP

2804 Midsummer Dr, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6147360
Active 81 Oakdale St, WINDERMERE

$2,197,000

▼ $2,000 DAVIS SHORES

81 Oakdale St, WINDERMERE

5 Beds 5 Baths 4,284 SqFt Single Family Residence MLS® # O6116858
Active 11840 Vinci Dr, WINDERMERE

$2,070,000

KEENES POINTE UN #11

11840 Vinci Dr, WINDERMERE

6 Beds 6 Baths 4,338 SqFt Single Family Residence MLS® # O6157396
New
Active 9922 Brentford Ct, WINDERMERE

$1,890,000

KEENES POINTE

9922 Brentford Ct, WINDERMERE

6 Beds 4 Baths 4,129 SqFt Single Family Residence MLS® # O6159616
Active 13036 Lake Roper Ct, WINDERMERE

$1,875,000

WINDERMERE POINTE AT LAKE ROPER

13036 Lake Roper Ct, WINDERMERE

5 Beds 6 Baths 4,044 SqFt Single Family Residence MLS® # O6146261
Active 6228 Roseate Spoonbill Dr, WINDERMERE

$1,875,000

WINDERMERE LNDGS FD-1

6228 Roseate Spoonbill Dr, WINDERMERE

8 Beds 5 Baths 4,751 SqFt Single Family Residence MLS® # O6158666

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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