Windermere 5+ Bedroom Homes for Sale

49 Days on Market

House for Sale

$30,000,000

7 bd · 14 ba · 51,000 sqft

9508 WINDY RIDGE ROAD, WINDERMERE, FL 34786

Newly Listed

House for Sale

$27,000,000

7 bd · 10 ba · 22,108 sqft

5603 MARLEON DRIVE, WINDERMERE, FL 34786

492 Days on Market

House for Sale

$17,250,000

7 bd · 9 ba · 10,649 sqft

11900 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786

Newly Listed

House for Sale

$15,900,000

7 bd · 9 ba · 14,068 sqft

6119 GROSVENOR SHORE DRIVE, WINDERMERE, FL 34786

Newly Listed

House for Sale

$15,500,000

10 bd · 17 ba · 13,425 sqft

12488 PARK AVENUE, WINDERMERE, FL 34786

20 Days on Market

House for Sale

$13,995,000

6 bd · 11 ba · 12,067 sqft

3057 PORTO LAGO COURT, WINDERMERE, FL 34786

56 Days on Market

House for Sale

$12,999,999

9 bd · 16 ba · 20,445 sqft

9621 WINDY RIDGE ROAD, WINDERMERE, FL 34786

56 Days on Market

House for Sale

$12,750,000

6 bd · 10 ba · 11,100 sqft

9832 LAUREL VALLEY DRIVE, WINDERMERE, FL 34786

Newly Listed

House for Sale

$12,350,000

7 bd · 10 ba · 11,465 sqft

9312 BLANCHE COVE DR, WINDERMERE, FL 34786

153 Days on Market

House for Sale

$11,900,000

6 bd · 10 ba · 9,770 sqft

9323 GLADYS GARDEN COURT, WINDERMERE, FL 34786

23 Days on Market

House for Sale

$10,200,000

6 bd · 9 ba · 6,457 sqft

728 FOREST STREET, WINDERMERE, FL 34786

270 Days on Market

House for Sale

$9,750,000

5 bd · 3 ba · 5,316 sqft

4226 DOWNEAST LANE, WINDERMERE, FL 34786

47 Days on Market

House for Sale

$7,999,000

6 bd · 9 ba · 8,038 sqft

9317 GLADYS GARDEN COURT, WINDERMERE, FL 34786

446 Days on Market

House for Sale

$7,795,000

7 bd · 10 ba · 8,362 sqft

9343 TIBET POINTE CIRCLE, WINDERMERE, FL 34786

13 Days on Market

House for Sale

$7,500,000

6 bd · 8 ba · 6,874 sqft

724 W 2ND AVENUE, WINDERMERE, FL 34786

186 Days on Market

House for Sale

$7,250,000

5 bd · 7 ba · 7,099 sqft

5074 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

Newly Listed

House for Sale

$7,000,000

5 bd · 6 ba · 7,158 sqft

6055 LOUISE COVE DRIVE, WINDERMERE, FL 34786

73 Days on Market

House for Sale

$6,995,000

5 bd · 8 ba · 7,529 sqft

9349 TIBET POINTE CIRCLE, WINDERMERE, FL 34786

Newly Listed

House for Sale

$6,900,000

5 bd · 7 ba · 6,300 sqft

9061 RON DEN LANE, WINDERMERE, FL 34786

16 Days on Market

House for Sale

$6,700,000

8 bd · 10 ba · 8,133 sqft

8342 BOYLA COURT, WINDERMERE, FL 34786

Newly Listed

House for Sale

$6,650,000

5 bd · 7 ba · 6,970 sqft

9921 LAKE LOUISE DRIVE, WINDERMERE, FL 34786

24 Days on Market

House for Sale

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 GLADYS GARDEN CT, WINDERMERE, FL 34786

178 Days on Market

House for Sale

$6,000,000

7 bd · 7 ba · 8,000 sqft

9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

16 Days on Market

House for Sale

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2ND AVENUE, WINDERMERE, FL 34786

Talk to a local agent

Looking at Windermere 5+ Bedroom Homes?

Tell us what you're after — we'll send matching homes, off-market options and recent sales, and set up private showings.

Matthew Gromadzki

Real Estate Broker

(786) 370-8570

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Live MLS inventory in Windermere, updated continuously. Showing homes with 5 or more bedrooms. Florida Lux Real Estate currently tracks 97 active listings here. MLS inventory updated October 11, 2026.