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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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FEATURED
Active 7417 Lake Albert Dr, WINDERMERE

$1,690,000

LAKE BURDEN

7417 Lake Albert Dr, WINDERMERE

6 Beds 7 Baths 5,006 SqFt Single Family Residence MLS® # S5135158
Active 11900 Lake Butler Blvd, WINDERMERE

$18,500,000

METCALF PARK REP

11900 Lake Butler Blvd, WINDERMERE

7 Beds 9 Baths 10,649 SqFt Single Family Residence MLS® # O6275556
Active 4226 Downeast Ln, WINDERMERE

$14,800,000

NA

4226 Downeast Ln, WINDERMERE

5 Beds 3 Baths 5,316 SqFt Single Family Residence MLS® # O6355233
Active 5525 Isleworth Country Club Dr, WINDERMERE

$14,250,000

ISLEWORTH

5525 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 9,511 SqFt Single Family Residence MLS® # O6304800
Active 9621 Windy Ridge Rd, WINDERMERE

$13,650,000

▼ $50,000 WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Single Family Residence MLS® # O6333091
Active 6149 Grosvenor Shore Dr, WINDERMERE

$9,999,000

KEENES POINTE

6149 Grosvenor Shore Dr, WINDERMERE

6 Beds 8 Baths 6,783 SqFt Single Family Residence MLS® # O6356355
Active 6137 Grosvenor Shore Dr, WINDERMERE

$8,995,000

▼ $505,000 KEENES POINTE

6137 Grosvenor Shore Dr, WINDERMERE

6 Beds 9 Baths 9,571 SqFt Single Family Residence MLS® # O6294487
Active 9343 Tibet Pointe Cir, WINDERMERE

$8,250,000

▼ $239,000 KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Single Family Residence MLS® # O6264629
Active 6507 Rosella Ct, WINDERMERE

$7,750,000

KEENES POINTE 46/104

6507 Rosella Ct, WINDERMERE

7 Beds 8 Baths 10,485 SqFt Single Family Residence MLS® # O6353035
Active 9259 Tibet Pointe Cir, WINDERMERE

$6,800,000

KEENES POINTE

9259 Tibet Pointe Cir, WINDERMERE

5 Beds 6 Baths 6,257 SqFt Single Family Residence MLS® # O6312645
Active 11103 Bridge House Rd, WINDERMERE

$6,799,000

▼ $451,000 RESERVE AT LAKE BUTLER SOUND 45/120

11103 Bridge House Rd, WINDERMERE

5 Beds 8 Baths 8,443 SqFt Single Family Residence MLS® # O6315165
Active 9639 Westover Roberts Rd, WINDERMERE

$6,395,000

GOTHA TOWN

9639 Westover Roberts Rd, WINDERMERE

5 Beds 9 Baths 11,861 SqFt Single Family Residence MLS® # O6341883
Active 9826 Laurel Valley Dr, WINDERMERE

$5,900,000

ISLEWORTH

9826 Laurel Valley Dr, WINDERMERE

5 Beds 6 Baths 7,491 SqFt Single Family Residence MLS® # O6345711
Active 12264 Montalcino Cir, WINDERMERE

$5,860,000

▼ $30,000 CASA DEL LAGO REP

12264 Montalcino Cir, WINDERMERE

4 Beds 7 Baths 7,872 SqFt Single Family Residence MLS® # O6325454
Active 1003 Down Reserve Ct, WINDERMERE

$5,499,999

LAKE DOWN RESERVE

1003 Down Reserve Ct, WINDERMERE

6 Beds 8 Baths 6,816 SqFt Single Family Residence MLS® # O6353952
Active 5199 Latrobe Dr, WINDERMERE

$5,494,000

ISLEWORTH

5199 Latrobe Dr, WINDERMERE

5 Beds 7 Baths 4,665 SqFt Single Family Residence MLS® # O6315618
Active 9721 Carillon Park Dr, WINDERMERE

$5,489,000

KEENES POINTE

9721 Carillon Park Dr, WINDERMERE

6 Beds 9 Baths 8,305 SqFt Single Family Residence MLS® # O6336879
Active 5243 Isleworth Country Club Dr, WINDERMERE

$5,325,000

ISLEWORTH

5243 Isleworth Country Club Dr, WINDERMERE

4 Beds 6 Baths 6,424 SqFt Single Family Residence MLS® # O6348067
Active 9733 Carillon Park Dr, WINDERMERE

$5,250,000

KEENES POINTE

9733 Carillon Park Dr, WINDERMERE

5 Beds 7 Baths 7,600 SqFt Single Family Residence MLS® # O6355029
Active 4089 Isabella Cir, WINDERMERE

$5,000,000

CASABELLA PH 2

4089 Isabella Cir, WINDERMERE

6 Beds 8 Baths 6,855 SqFt Single Family Residence MLS® # O6273887
Active 9575 Westover Roberts Rd, WINDERMERE

$4,925,000

GOTHA TOWN

9575 Westover Roberts Rd, WINDERMERE

7 Beds 8 Baths 8,931 SqFt Single Family Residence MLS® # O6357873
Active 5036 Latrobe Dr, WINDERMERE

$4,900,000

ISLEWORTH

5036 Latrobe Dr, WINDERMERE

5 Beds 5 Baths 5,548 SqFt Single Family Residence MLS® # O6346003
Active 225 Magnolia St, WINDERMERE

$4,899,000

WINDERMERE TOWN

225 Magnolia St, WINDERMERE

7 Beds 11 Baths 5,935 SqFt Single Family Residence MLS® # O6292745
Active 12540 Park Ave, WINDERMERE

$4,650,000

CHAINE DE LAC

12540 Park Ave, WINDERMERE

5 Beds 6 Baths 7,183 SqFt Single Family Residence MLS® # O6346858
Active 5500 W Lake Butler Rd, WINDERMERE

$4,299,999

▼ $100,000 WEST LAKE BUTLER ESTATES

5500 W Lake Butler Rd, WINDERMERE

8 Beds 6 Baths 7,000 SqFt Single Family Residence MLS® # TB8382641
Active 11002 Lake Butler Blvd, WINDERMERE

$4,200,000

METCALF PARK REP

11002 Lake Butler Blvd, WINDERMERE

5 Beds 8 Baths 6,248 SqFt Single Family Residence MLS® # O6284922
Active 12132 Montalcino Cir, WINDERMERE

$4,199,000

CASA DEL LAGO REP

12132 Montalcino Cir, WINDERMERE

6 Beds 7 Baths 5,709 SqFt Single Family Residence MLS® # O6319854
Active 801 W 2nd Ave, WINDERMERE

$4,150,000

▼ $100,000 ALADAR ON LAKE BUTLER

801 W 2nd Ave, WINDERMERE

5 Beds 7 Baths 5,639 SqFt Single Family Residence MLS® # O6290240
Active 9648 Mccormick Pl, WINDERMERE

$3,800,000

ISLEWORTH

9648 Mccormick Pl, WINDERMERE

3 Beds 4 Baths 4,751 SqFt Single Family Residence MLS® # O6346918
Active 12812 Jacob Grace Ct, WINDERMERE

$3,775,000

▼ $24,000 TILDENS GROVE PH 01 47/65

12812 Jacob Grace Ct, WINDERMERE

4 Beds 5 Baths 6,054 SqFt Single Family Residence MLS® # V4943735
Active 2844 Marquesas Ct, WINDERMERE

$3,700,000

▼ $200,000 LAKE CRESCENT RESERVE

2844 Marquesas Ct, WINDERMERE

4 Beds 3 Baths 5,365 SqFt Single Family Residence MLS® # O6350786
Active 4812 Alexandra Garden Ct, WINDERMERE

$3,699,000

ISLEWORTH

4812 Alexandra Garden Ct, WINDERMERE

3 Beds 5 Baths 4,262 SqFt Single Family Residence MLS® # O6339134
Active 5024 Sawyer Cove Way, WINDERMERE

$3,600,000

SAWYER SOUND

5024 Sawyer Cove Way, WINDERMERE

5 Beds 7 Baths 5,501 SqFt Single Family Residence MLS® # O6348086
Active 6130 Grosvenor Shore Dr, WINDERMERE

$3,500,000

KEENES POINTE

6130 Grosvenor Shore Dr, WINDERMERE

4 Beds 5 Baths 4,676 SqFt Single Family Residence MLS® # O6361099
Active 13305 Bellaria Cir, WINDERMERE

$3,490,000

▼ $210,000 BELLARIA

13305 Bellaria Cir, WINDERMERE

6 Beds 8 Baths 6,930 SqFt Single Family Residence MLS® # O6286539
Active 9731 Chestnut Ridge Dr, WINDERMERE

$3,400,000

ISLEWORTH

9731 Chestnut Ridge Dr, WINDERMERE

4 Beds 4 Baths 4,877 SqFt Single Family Residence MLS® # O6336655
Active 2012 Bellamere Ct, WINDERMERE

$3,350,000

▼ $25,000 BELLA VITA ESTATES

2012 Bellamere Ct, WINDERMERE

5 Beds 6 Baths 4,701 SqFt Single Family Residence MLS® # O6333400
Active 4301 Down Point Ln, WINDERMERE

$3,350,000

DOWN POINT SUB

4301 Down Point Ln, WINDERMERE

5 Beds 4 Baths 6,834 SqFt Single Family Residence MLS® # O6351950
Active 6161 Grosvenor Shore Dr, WINDERMERE

$3,300,000

▲ $400,000 KEENE'S POINTE

6161 Grosvenor Shore Dr, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6182683
Active 4711 Joanna Garden Ct, WINDERMERE

$3,250,000

ISLEWORTH

4711 Joanna Garden Ct, WINDERMERE

3 Beds 4 Baths 4,089 SqFt Single Family Residence MLS® # O6359789
Active 13448 Bellaria Cir, WINDERMERE

$3,250,000

BELLARIA

13448 Bellaria Cir, WINDERMERE

6 Beds 7 Baths 6,308 SqFt Single Family Residence MLS® # O6346484
Active 13161 Lake Butler Blvd, WINDERMERE

$3,200,000

LAKE ROPER POINTE

13161 Lake Butler Blvd, WINDERMERE

5 Beds 5 Baths 4,500 SqFt Single Family Residence MLS® # TB8421056
Active 2 Chase Rd, WINDERMERE

$3,200,000

WINDERMERE

2 Chase Rd, WINDERMERE

4 Beds 5 Baths 3,889 SqFt Single Family Residence MLS® # O6345197
Active 9151 Tibet Pointe Cir, WINDERMERE

$3,200,000

KEENES POINTE

9151 Tibet Pointe Cir, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6275446
Active 13125 Casabella Dr, WINDERMERE

$3,194,000

▼ $1,000 CASABELLA

13125 Casabella Dr, WINDERMERE

5 Beds 6 Baths 7,561 SqFt Single Family Residence MLS® # O6297797
Active 12213 Park Ave, WINDERMERE

$3,000,000

CHAINE DE LAC

12213 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6351906
Active 12923 Water Point Blvd, WINDERMERE

$2,999,999

WATERFORD POINTE

12923 Water Point Blvd, WINDERMERE

5 Beds 5 Baths 5,005 SqFt Single Family Residence MLS® # O6350408
Active 5067 Sawyer Cove Way, WINDERMERE

$2,999,500

SAWYER SOUND

5067 Sawyer Cove Way, WINDERMERE

5 Beds 4 Baths 3,461 SqFt Single Family Residence MLS® # O6357042

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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