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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
• $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

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Active

$30,000,000

N/A

9508 Windy Ridge Rd, WINDERMERE

7 Beds 14 Baths 51,000 SqFt Residential Single Family Residence MLS® # O6388674

Active

$27,000,000

NA

5603 Marleon Dr, WINDERMERE

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

Active

$17,250,000

▼ $1,250,000 METCALF PARK REP

11900 Lake Butler Blvd, WINDERMERE

7 Beds 9 Baths 10,649 SqFt Residential Single Family Residence MLS® # O6275556

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

$13,430,000

▼ $100,000 WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Residential Single Family Residence MLS® # O6400740

Active

$12,500,000

▼ $1,495,000 ISLEWORTH

9323 Gladys Garden Ct, WINDERMERE

6 Beds 10 Baths 9,770 SqFt Residential Single Family Residence MLS® # O6381880

Active

$10,900,000

▲ $901,000 KEENES POINTE

6149 Grosvenor Shore Dr, WINDERMERE

6 Beds 8 Baths 6,783 SqFt Residential Single Family Residence MLS® # O6356355

Active

$10,500,000

▼ $1,300,000

4226 Downeast Ln, WINDERMERE

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

Active

$10,500,000

▼ $1,300,000 NA

4226 Downeast Ln, WINDERMERE

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

Active

$7,595,000

ISLEWORTH

5074 Isleworth Country Club Dr, WINDERMERE

5 Beds 7 Baths 6,937 SqFt Residential Single Family Residence MLS® # O6373191

Active

$7,400,000

KEENES POINTE

9349 Tibet Pointe Cir, WINDERMERE

5 Beds 8 Baths 7,529 SqFt Residential Single Family Residence MLS® # O6404415

Active

$6,980,000

ISLEWORTH

5186 Vardon Dr, WINDERMERE

4 Beds 5 Baths 4,739 SqFt Residential Single Family Residence MLS® # O6382040

New

Active

$6,950,000

ISLEWORTH

6462 Deacon Cir, WINDERMERE

5 Beds 6 Baths 7,178 SqFt Residential Single Family Residence MLS® # O6407107

Active

$6,000,000

▼ $150,000 ISLEWORTH

9725 Chestnut Ridge Dr, WINDERMERE

7 Beds 7 Baths 8,000 SqFt Residential Single Family Residence MLS® # O6370294

Active

$5,900,000

▼ $495,000 GOTHA TOWN

9639 Westover Roberts Rd, WINDERMERE

5 Beds 9 Baths 11,861 SqFt Residential Single Family Residence MLS® # O6341883

Active

$5,760,000

▼ $100,000 CASA DEL LAGO REP

12264 Montalcino Cir, WINDERMERE

4 Beds 7 Baths 7,872 SqFt Residential Single Family Residence MLS® # O6404587

Active

$5,500,000

LAKE OLIVIA RESERVE

1330 Lake Olivia, WINDERMERE

6 Beds 8 Baths 6,442 SqFt Residential Single Family Residence MLS® # S5144942

Active

$5,500,000

ISLEWORTH

5138 Fairway Oaks Dr, WINDERMERE

4 Beds 5 Baths 4,330 SqFt Residential Single Family Residence MLS® # O6401757

Active

$5,250,000

▼ $150,000 ISLEWORTH WEST

6117 Louise Cove Dr, WINDERMERE

4 Beds 5 Baths 5,752 SqFt Residential Single Family Residence MLS® # O6372197

Active

$5,100,000

▼ $225,000 ISLEWORTH

5243 Isleworth Country Club Dr, WINDERMERE

4 Beds 6 Baths 6,424 SqFt Residential Single Family Residence MLS® # O6348067

Active

$5,000,000

▼ $489,000 KEENES POINTE

9721 Carillon Park Dr, WINDERMERE

6 Beds 9 Baths 8,305 SqFt Residential Single Family Residence MLS® # O6336879

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

New Open House

Active

$4,700,000

WEST LAKE BUTLER ESTATES

5500 W Lake Butler Rd, WINDERMERE

8 Beds 6 Baths 7,000 SqFt Residential

Open House

Wed, May 20th, 2026 @ 6pm - 8pm

Single Family Residence MLS® # O6408637

Active

$4,690,000

▲ $221,000 GARDENS/ISLEWORTH UN #2

4906 Aviva Garden Ct, WINDERMERE

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

Active

$4,650,000

LAKE DOWN RESERVE

1009 Down Reserve Ct, WINDERMERE

5 Beds 8 Baths 7,940 SqFt Residential Single Family Residence MLS® # O6346638

Active

$4,599,000

CHAINE DU LAC

12540 Park Ave, WINDERMERE

5 Beds 6 Baths 7,740 SqFt Residential Single Family Residence MLS® # O6381869

Active

$4,450,000

GARDENS/ISLEWORTH

9144 Isleworth Gardens Dr, WINDERMERE

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

Active

$4,399,000

KEENES POINTE

6120 Greatwater Dr, WINDERMERE

5 Beds 6 Baths 5,580 SqFt Residential Single Family Residence MLS® # O6404574

Active

$4,395,000

CHAINE DU LAC

12418 Park Ave, WINDERMERE

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

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

$3,995,000

ALADAR ON LAKE BUTLER

801 W 2nd Ave, WINDERMERE

5 Beds 7 Baths 5,639 SqFt Residential Single Family Residence MLS® # O6375693

Active

$3,900,000

▲ $2,300,000 WINDERMERE TOWN

212 W 1st Ave, WINDERMERE

5 Beds 5 Baths 3,800 SqFt Residential Single Family Residence MLS® # S5148430

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

$3,790,000

▼ $160,000 CASA DEL LAGO REP

12132 Montalcino Cir, WINDERMERE

6 Beds 7 Baths 5,709 SqFt Residential Single Family Residence MLS® # O6319854

Active

$3,725,000

LAKE BUTLER PARK PT REP

58 Main St, WINDERMERE

5 Beds 4 Baths 4,875 SqFt Residential Single Family Residence MLS® # O6370886

Active

$3,700,000

KEENES POINTE 46/104

6857 Valhalla Way, WINDERMERE

5 Beds 7 Baths 7,153 SqFt Residential Single Family Residence MLS® # S5147781

Active

$3,699,888

▼ $25,112 TILDENS GROVE PH 01 47/65

12812 Jacob Grace Ct, WINDERMERE

4 Beds 6 Baths 6,054 SqFt Residential Single Family Residence MLS® # V4943735

Active

$3,699,000

ISLEWORTH

4812 Alexandra Garden Ct, WINDERMERE

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

Active

$3,500,000

DAVIS SHORES

43 Main St, WINDERMERE

4 Beds 4 Baths 2,500 SqFt Residential Single Family Residence MLS® # O6387626

Active

$3,499,999

ISLEWORTH

5001 Latrobe Dr, WINDERMERE

5 Beds 5 Baths 4,417 SqFt Residential Single Family Residence MLS® # O6389183

Open House

Active

$3,450,000

▼ $25,000 LAKES

10577 Down Lakeview Cir, WINDERMERE

4 Beds 4 Baths 5,273 SqFt Residential

Open House

Sat, May 23rd, 2026 @ 11am - 1pm

Single Family Residence MLS® # O6377244

Active

$3,400,000

ISLEWORTH

9731 Chestnut Ridge Dr, WINDERMERE

4 Beds 4 Baths 4,877 SqFt Residential Single Family Residence MLS® # O6336655

Active

$3,390,000

▼ $300,000 ISLEWORTH

5050 Isleworth Country Club Dr, WINDERMERE

4 Beds 5 Baths 3,365 SqFt Residential Single Family Residence MLS® # O6372348

Active

$3,299,000

▼ $150,000 ISLEWORTH

5145 Latrobe Dr, WINDERMERE

4 Beds 5 Baths 4,512 SqFt Residential Single Family Residence MLS® # O6382287

Active

$3,200,000

LAKE ROPER POINTE

13161 Lake Butler Blvd, WINDERMERE

5 Beds 5 Baths 4,500 SqFt Residential Single Family Residence MLS® # TB8421056

Active

$3,200,000

ISLEWORTH

4819 Alexandra Garden Ct, WINDERMERE

4 Beds 5 Baths 3,745 SqFt Residential Single Family Residence MLS® # O6330108

Active

$3,200,000

WINDERMERE

2 Chase Rd, WINDERMERE

4 Beds 5 Baths 3,889 SqFt Residential Single Family Residence MLS® # O6345197

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