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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 6004 Cartmel Ln, WINDERMERE

$30,000,000

RESERVE AT LAKE BUTLER SOUND

6004 Cartmel Ln, WINDERMERE

9 Beds 17 Baths 20,240 SqFt Single Family Residence MLS® # O6162188
Active 9306 Blanche Cove Dr, WINDERMERE

$15,500,000

ISLEWORTH 7TH AMD

9306 Blanche Cove Dr, WINDERMERE

6 Beds 8 Baths 14,856 SqFt Single Family Residence MLS® # O6180696
Active 9621 Windy Ridge Rd, WINDERMERE

$13,950,000

WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Single Family Residence MLS® # O6184943
Active 4200 Down Point Ln, WINDERMERE

$13,900,000

DOWN POINT SUB

4200 Down Point Ln, WINDERMERE

6 Beds 9 Baths 14,435 SqFt Single Family Residence MLS® # O6176070
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 5507 Worsham Ct, WINDERMERE

$8,650,000

ISLEWORTH

5507 Worsham Ct, WINDERMERE

5 Beds 11 Baths 10,200 SqFt Single Family Residence MLS® # O6180706
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 9313 Tibet Pointe Cir, WINDERMERE

$7,999,000

KEENES POINTE 46/104

9313 Tibet Pointe Cir, WINDERMERE

6 Beds 8 Baths 8,792 SqFt Single Family Residence MLS® # O6170422
Active 6131 Grosvenor Shore Dr, WINDERMERE

$7,200,000

KEENES POINTE

6131 Grosvenor Shore Dr, WINDERMERE

7 Beds 9 Baths 8,596 SqFt Single Family Residence MLS® # O6189962
Active 6462 Deacon Cir, WINDERMERE

$6,950,000

ISLEWORTH

6462 Deacon Cir, WINDERMERE

5 Beds 6 Baths 7,178 SqFt Single Family Residence MLS® # O6173721
Active 5190 Latrobe Dr, WINDERMERE

$6,300,000

ISLEWORTH

5190 Latrobe Dr, WINDERMERE

5 Beds 8 Baths 7,191 SqFt Single Family Residence MLS® # O6172519
Active 9139 Tibet Pointe Cir, WINDERMERE

$5,995,000

▼ $500,000 KEENES POINTE 46/104

9139 Tibet Pointe Cir, WINDERMERE

6 Beds 9 Baths 10,341 SqFt Single Family Residence MLS® # O6163962
Active 11449 Waterstone Loop Dr, WINDERMERE

$5,950,000

▼ $550,000 WATERSTONE

11449 Waterstone Loop Dr, WINDERMERE

6 Beds 6 Baths 6,235 SqFt Single Family Residence MLS® # O6170332
Active 10821 Bayshore Dr, WINDERMERE

$5,950,000

BAYSHORE ESTATES

10821 Bayshore Dr, WINDERMERE

4 Beds 6 Baths 5,275 SqFt Single Family Residence MLS® # O6189960
Active 526 Butler St, WINDERMERE

$5,755,000

WINDERMERE TOWN

526 Butler St, WINDERMERE

4 Beds 6 Baths 6,688 SqFt Single Family Residence MLS® # O6178229
Active 12540 Park Ave, WINDERMERE

$5,750,000

▼ $50,000 CHAINE DE LAC

12540 Park Ave, WINDERMERE

5 Beds 7 Baths 7,736 SqFt Single Family Residence MLS® # O6151810
Active 5174 Vardon Dr, WINDERMERE

$5,500,000

▼ $475,000 ISLEWORTH

5174 Vardon Dr, WINDERMERE

6 Beds 9 Baths 10,701 SqFt Single Family Residence MLS® # O6143716
Active 6120 Kirkstone Ln, WINDERMERE

$5,400,000

▼ $799,000 RESERVE AT LAKE BUTLER SOUND

6120 Kirkstone Ln, WINDERMERE

5 Beds 7 Baths 6,972 SqFt Single Family Residence MLS® # O6172400
Active 9205 Tibet Pointe Cir, WINDERMERE

$5,350,000

KEENES POINTE 46/104

9205 Tibet Pointe Cir, WINDERMERE

5 Beds 10 Baths 8,259 SqFt Single Family Residence MLS® # O6166914
Active 9844 Laurel Valley Dr, WINDERMERE

$5,300,000

ISLEWORTH

9844 Laurel Valley Dr, WINDERMERE

5 Beds 6 Baths 5,613 SqFt Single Family Residence MLS® # O6173216
Active 6109 Orta Ct, WINDERMERE

$5,099,000

WATERSTONE

6109 Orta Ct, WINDERMERE

5 Beds 7 Baths 5,895 SqFt Single Family Residence MLS® # O6161019
Active 11217 Bridge House Rd, WINDERMERE

$4,980,000

▼ $370,000 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 11606 Lake Butler Blvd, WINDERMERE

$4,975,000

▼ $520,000 METCALF PARK REP

11606 Lake Butler Blvd, WINDERMERE

6 Beds 8 Baths 7,400 SqFt Single Family Residence MLS® # O6181136
Active 5410 Monterrey Club Ct, WINDERMERE

$4,950,000

▼ $150,000 ISLEWORTH 01 AMD

5410 Monterrey Club Ct, WINDERMERE

6 Beds 8 Baths 6,665 SqFt Single Family Residence MLS® # O6178971
Active 4233 Down Point Ln, WINDERMERE

$4,950,000

SUNSET BAY

4233 Down Point Ln, WINDERMERE

6 Beds 7 Baths 6,478 SqFt Single Family Residence MLS® # O6188162
Active 5092 Isleworth Country Club Dr, WINDERMERE

$4,495,000

▼ $505,000 ISLEWORTH

5092 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 6,115 SqFt Single Family Residence MLS® # O6167834
Active 5084 Isleworth Country Club Dr, WINDERMERE

$4,350,000

▼ $145,000 ISLEWORTH

5084 Isleworth Country Club Dr, WINDERMERE

6 Beds 8 Baths 7,159 SqFt Single Family Residence MLS® # O6140732
Active 9725 Chestnut Ridge Dr, WINDERMERE

$4,335,000

ISLEWORTH

9725 Chestnut Ridge Dr, WINDERMERE

5 Beds 6 Baths 7,223 SqFt Single Family Residence MLS® # O6192766
Active 9720 Nearwater Pl, WINDERMERE

$4,250,000

WINDERMERE DOWNS

9720 Nearwater Pl, WINDERMERE

4 Beds 6 Baths 6,119 SqFt Single Family Residence MLS® # O6194849
Active 6760 Valhalla Way, WINDERMERE

$3,999,999

KEENES POINTE 46/104

6760 Valhalla Way, WINDERMERE

5 Beds 7 Baths 6,055 SqFt Single Family Residence MLS® # O6189834
Active 9514 Lavill Ct, WINDERMERE

$3,999,000

LAKE DOWN VILLAGE

9514 Lavill Ct, WINDERMERE

5 Beds 4 Baths 4,869 SqFt Single Family Residence MLS® # O6193315
Active 9151 Tibet Pointe Cir, WINDERMERE

$3,900,000

KEENES POINTE

9151 Tibet Pointe Cir, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6167488
Active 4047 Isabella Cir, WINDERMERE

$3,799,000

▼ $71,000 CASABELLA PH 2

4047 Isabella Cir, WINDERMERE

6 Beds 8 Baths 8,372 SqFt Single Family Residence MLS® # O6158850
Active 4272 Isabella Cir, WINDERMERE

$3,650,000

▼ $249,000 CASABELLA

4272 Isabella Cir, WINDERMERE

7 Beds 9 Baths 6,544 SqFt Single Family Residence MLS® # O6172988
Active 4261 Isabella Cir, WINDERMERE

$3,575,500

▼ $123,500 CASABELLA

4261 Isabella Cir, WINDERMERE

6 Beds 9 Baths 7,129 SqFt Single Family Residence MLS® # O6164738
Active 800 West 2nd Ave, WINDERMERE

$3,500,000

▼ $400,000 ALADAR ON LAKE BUTLER

800 West 2nd Ave, WINDERMERE

5 Beds 5 Baths 5,111 SqFt Single Family Residence MLS® # O6141389
New
Active 11030 Bridge House Rd, WINDERMERE

$3,499,999

RESERVE AT LAKE BUTLER SOUND 45/120

11030 Bridge House Rd, WINDERMERE

6 Beds 9 Baths 7,718 SqFt Single Family Residence MLS® # O6196254
Active 6030 Greatwater Dr, WINDERMERE

$3,495,000

▼ $31,455,000 KEENES POINTE

6030 Greatwater Dr, WINDERMERE

6 Beds 7 Baths 6,490 SqFt Single Family Residence MLS® # O6194035
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 5127 Latrobe Dr, WINDERMERE

$3,400,000

▼ $550,000 ISLEWORTH

5127 Latrobe Dr, WINDERMERE

7 Beds 8 Baths 6,933 SqFt Single Family Residence MLS® # O6170314
Active 11617 Waterstone Loop Dr, WINDERMERE

$3,300,000

WATERSTONE

11617 Waterstone Loop Dr, WINDERMERE

4 Beds 5 Baths 4,957 SqFt Single Family Residence MLS® # O6177372
Active 325 Magnolia St, WINDERMERE

$3,148,000

WINDERMERE TOWN

325 Magnolia St, WINDERMERE

4 Beds 3 Baths 3,975 SqFt Single Family Residence MLS® # O6182702
Active 6161 Grosvenor Shore Dr, WINDERMERE

$3,099,000

KEENE'S POINTE

6161 Grosvenor Shore Dr, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6182683
Active 6132 Payne Stewart Dr, WINDERMERE

$2,999,000

▼ $200,000 ISLEWORTH

6132 Payne Stewart Dr, WINDERMERE

3 Beds 4 Baths 2,848 SqFt Single Family Residence MLS® # O6183633
Active 5379 Isleworth Country Club Dr, WINDERMERE

$2,997,000

ISLEWORTH

5379 Isleworth Country Club Dr, WINDERMERE

4 Beds 4 Baths 3,872 SqFt Single Family Residence MLS® # O6172675
Active 4011 Isabella Cir, WINDERMERE

$2,995,000

▼ $254,999 CASABELLA PH 2

4011 Isabella Cir, WINDERMERE

5 Beds 7 Baths 5,418 SqFt Single Family Residence MLS® # O6172666
Active 4704 Joanna Garden Ct, WINDERMERE

$2,950,000

▼ $250,000 ISLEWORTH

4704 Joanna Garden Ct, WINDERMERE

3 Beds 5 Baths 4,261 SqFt Single Family Residence MLS® # O6175127
Active 628 Butler St, WINDERMERE

$2,888,000

▼ $412,000 MARSH SUB

628 Butler St, WINDERMERE

6 Beds 6 Baths 4,486 SqFt Single Family Residence MLS® # O6163405

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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