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Windermere, Florida 34786: Located in Orange County, Windermere is synonymous with lakeside elegance, tree-lined streets, and a luxurious lifestyle. Known for its chain of lakes and upscale residences, this charming town offers a serene environment with a touch of sophistication, all while being close to Central Florida's major attractions and urban conveniences.

Search by ZIP Code - 34786

• All Listings
• $100,000 - $200,000
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• $600,000 - $700,000
• $700,000 - $800,000
• $800,000 - $900,000
• $900,000 - $1,000,000
• Over $1,000,000

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Bathrooms

Price Range

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Active

$27,000,000

NA

5603 Marleon Dr, WINDERMERE

7 Beds 10 Baths 22,108 SqFt Residential Single Family Residence MLS® # O6404938

Active

$15,900,000

KEENES POINT

6119 Grosvenor Shore Dr, WINDERMERE

8 Beds 11 Baths 14,068 SqFt Residential Single Family Residence MLS® # O6421205

Active

$15,500,000

CHAINE DU LAC

12488 Park Ave, WINDERMERE

10 Beds 17 Baths 13,425 SqFt Residential Single Family Residence MLS® # O6395291

Active

$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

$12,350,000

ISLEWORTH 5TH AMD

9312 Blanche Cove Dr, WINDERMERE

7 Beds 10 Baths 11,465 SqFt Residential Single Family Residence MLS® # O6407102

Active

$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

$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

$10,200,000

WINDERMERE TOWN

728 Forest St, WINDERMERE

6 Beds 9 Baths 6,457 SqFt Residential Single Family Residence MLS® # O6411906

Active

$9,750,000

▼ $750,000

4226 Downeast Ln, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6367852

Active

$9,750,000

▼ $750,000 NA

4226 Downeast Ln, WINDERMERE

5 Beds 3 Baths 5,316 SqFt Residential Single Family Residence MLS® # O6355233

Active

$8,695,000

CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6416090

Active

$7,695,000

▼ $100,000 KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Residential Single Family Residence MLS® # O6264629

Active

$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

New

Active

$7,200,000

ISLEWORTH

5373 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 5,993 SqFt Residential Single Family Residence MLS® # O6439156

Active

$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

Active

$6,900,000

DOWN ACRES ESTATES

9061 Ron Den Ln, WINDERMERE

5 Beds 7 Baths 6,300 SqFt Residential Single Family Residence MLS® # O6417446

Active

$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

$6,700,000

KEENES POINTE

8342 Boyla Ct, WINDERMERE

8 Beds 10 Baths 8,133 SqFt Residential Single Family Residence MLS® # O6422852

Active

$6,650,000

ISLEWORTH

9921 Lake Louise Dr, WINDERMERE

5 Beds 7 Baths 6,970 SqFt Residential Single Family Residence MLS® # O6429164

Active

$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

$5,999,000

ALADAR ON LAKE BUTLER

800 W 2nd Ave, WINDERMERE

5 Beds 5 Baths 5,511 SqFt Residential Single Family Residence MLS® # O6422976

Active

$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

$5,500,000

LAKE OLIVIA RESERVE

1330 Lake Olivia, WINDERMERE

6 Beds 8 Baths 6,442 SqFt Residential Single Family Residence MLS® # S5155388

Active

$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

$5,300,000

ISLEWORTH

5199 Latrobe Dr, WINDERMERE

6 Beds 7 Baths 4,665 SqFt Residential Single Family Residence MLS® # O6409961

New

Active

$5,250,000

▲ $750,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439497

Active

$4,995,000

SUNSET BAY

5070 Down Point Ln, WINDERMERE

6 Beds 7 Baths 7,349 SqFt Residential Single Family Residence MLS® # O6385276

Active

$4,850,000

▼ $75,000 GOTHA TOWN

9575 Westover Roberts Rd, WINDERMERE

7 Beds 8 Baths 8,931 SqFt Residential Single Family Residence MLS® # O6357873

Active

$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

New

Active

$4,750,000

▲ $500,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439342

Active

$4,495,000

KEENES POINTE 46/104

6719 Valhalla Way, WINDERMERE

4 Beds 7 Baths 6,159 SqFt Residential Single Family Residence MLS® # O6428554

Active

$4,395,000

CHAINE DU LAC

12418 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6370377

New

Active

$4,250,000

▼ $250,000

Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6439500

Active

$4,100,000

▼ $200,000 ISLEWORTH

9144 Isleworth Gardens Dr, WINDERMERE

3 Beds 5 Baths 5,004 SqFt Residential Single Family Residence MLS® # O6397842

Active

$3,999,999

▼ $200,001 METCALF PARK REP

11002 Lake Butler Blvd, WINDERMERE

5 Beds 8 Baths 6,248 SqFt Residential Single Family Residence MLS® # O6284922

Active

$3,990,000

▼ $200,000 GARDENS/ISLEWORTH UN #2

4906 Aviva Garden Ct, WINDERMERE

3 Beds 5 Baths 6,236 SqFt Residential Single Family Residence MLS® # O6400218

Active

$3,990,000

▼ $10,000 CASABELLA

4201 Isabella Cir, WINDERMERE

6 Beds 7 Baths 6,896 SqFt Residential Single Family Residence MLS® # O6430081

Active

$3,900,000

▼ $200,000 ISLEWORTH

5151 Latrobe Dr, WINDERMERE

4 Beds 5 Baths 5,301 SqFt Residential Single Family Residence MLS® # O6392380

Active

$3,750,000

GOTHA TOWN

9960 6th St, WINDERMERE

5 Beds 6 Baths 6,182 SqFt Residential Single Family Residence MLS® # O6412077

Active

$3,700,000

CASABELLA

4302 Isabella Cir, WINDERMERE

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

Active

$3,699,000

ISLEWORTH

4812 Alexandra Garden Ct, WINDERMERE

3 Beds 5 Baths 4,262 SqFt Residential Single Family Residence MLS® # O6339134

Active

$3,599,000

CASABELLA PH 2

3986 Isabella Cir, WINDERMERE

5 Beds 7 Baths 5,342 SqFt Residential Single Family Residence MLS® # O6432946

Active

$3,500,000

ISLEWORTH

5524 Worsham Ct, WINDERMERE

4 Beds 6 Baths 7,669 SqFt Residential Single Family Residence MLS® # O6430755

Active

$3,400,000

NONE

9679 Westover Roberts Rd, WINDERMERE

6 Beds 7 Baths 5,666 SqFt Residential Single Family Residence MLS® # S5154885

Active

$3,400,000

ISLEWORTH

5379 Isleworth Country Club Dr, WINDERMERE

4 Beds 4 Baths 3,872 SqFt Residential Single Family Residence MLS® # O6438449

New

Active

$3,300,000

WINDERMERE TOWN

515 W 2nd Ave, WINDERMERE

4 Beds 6 Baths 3,966 SqFt Residential Single Family Residence MLS® # O6439554

Active

$3,300,000

▼ $500,000 LAKE BUTLER ESTATES

11539 Lake Butler Blvd, WINDERMERE

5 Beds 5 Baths 5,018 SqFt Residential Single Family Residence MLS® # O6416913

New

Active

$3,290,000

CASABELLA

4243 Isabella Cir, WINDERMERE

5 Beds 7 Baths 5,502 SqFt Residential Single Family Residence MLS® # O6439995

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