Windermere Homes for Sale under $500K

36 listings
13424 HOPKINTON CT, WINDERMERE, FL 34786
38 Days on Market

House for Sale

$500,000

4 bd · 3 ba · 2,190 sqft

13424 HOPKINTON CT, WINDERMERE, FL 34786

8386 IRON MOUNTAIN TRAIL, WINDERMERE, FL 34786
Newly Listed

Townhome for Sale

$485,000

3 bd · 3 ba · 1,631 sqft

8386 IRON MOUNTAIN TRAIL, WINDERMERE, FL 34786

8266 BRYCE CANYON AVENUE, WINDERMERE, FL 34786
49 Days on Market

House for Sale

$479,500

3 bd · 3 ba · 1,825 sqft

8266 BRYCE CANYON AVENUE, WINDERMERE, FL 34786

8272 BRYCE CANYON AVENUE, WINDERMERE, FL 34786
151 Days on Market

House for Sale

$479,000

3 bd · 3 ba · 1,888 sqft

8272 BRYCE CANYON AVENUE, WINDERMERE, FL 34786

11861 VERMILLION AVENUE, WINDERMERE, FL 34786
60 Days on Market

Townhome for Sale

$475,000

3 bd · 3 ba · 1,600 sqft

11861 VERMILLION AVENUE, WINDERMERE, FL 34786

13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786
33 Days on Market

House for Sale

$474,900

3 bd · 3 ba · 1,636 sqft

13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786

13755 BRAVANTE ALLEY, WINDERMERE, FL 34786
121 Days on Market

Townhome for Sale

$465,000

3 bd · 3 ba · 2,091 sqft

13755 BRAVANTE ALLEY, WINDERMERE, FL 34786

12353 VIA DERNA PLACE, WINDERMERE, FL 34786
70 Days on Market

Townhome for Sale

$460,000

3 bd · 3 ba · 1,974 sqft

12353 VIA DERNA PLACE, WINDERMERE, FL 34786

11429 BROWNSTONE STREET, WINDERMERE, FL 34786
14 Days on Market

Townhome for Sale

$460,000

4 bd · 3 ba · 1,910 sqft

11429 BROWNSTONE STREET, WINDERMERE, FL 34786

7327 MILLSTONE STREET, WINDERMERE, FL 34786
101 Days on Market

Townhome for Sale

$459,000

3 bd · 3 ba · 1,531 sqft

7327 MILLSTONE STREET, WINDERMERE, FL 34786

12305 VIA DERNA PLACE, WINDERMERE, FL 34786
190 Days on Market

Townhome for Sale

$450,000

3 bd · 3 ba · 1,891 sqft

12305 VIA DERNA PLACE, WINDERMERE, FL 34786

7060 VENTNOR DRIVE, WINDERMERE, FL 34786
Newly Listed

Townhome for Sale

$444,900

3 bd · 3 ba · 1,642 sqft

7060 VENTNOR DRIVE, WINDERMERE, FL 34786

13712 SUMMERPORT VILLAGE PARKWAY, WINDERMERE, FL 34786
93 Days on Market

Townhome for Sale

$444,900

3 bd · 3 ba · 1,997 sqft

13712 SUMMERPORT VILLAGE PARKWAY, WINDERMERE, FL 34786

7612 FAIRGROVE AVENUE, WINDERMERE, FL 34786
35 Days on Market

Townhome for Sale

$440,000

3 bd · 3 ba · 1,742 sqft

7612 FAIRGROVE AVENUE, WINDERMERE, FL 34786

12988 BORLAND STREET, WINDERMERE, FL 34786
Newly Listed

Townhome for Sale

$435,000

3 bd · 3 ba · 1,460 sqft

12988 BORLAND STREET, WINDERMERE, FL 34786

8866 HERENCIA ALY, WINDERMERE, FL 34786
79 Days on Market

Townhome for Sale

$430,000

3 bd · 3 ba · 1,577 sqft

8866 HERENCIA ALY, WINDERMERE, FL 34786

12357 VIA DERNA PLACE, WINDERMERE, FL 34786
34 Days on Market

Townhome for Sale

$430,000

3 bd · 3 ba · 1,919 sqft

12357 VIA DERNA PLACE, WINDERMERE, FL 34786

7752 RIGBY STREET, WINDERMERE, FL 34786
Newly Listed

Townhome for Sale

$425,000

3 bd · 3 ba · 1,335 sqft

7752 RIGBY STREET, WINDERMERE, FL 34786

7435 RIPPLEPOINTE WAY, WINDERMERE, FL 34786
65 Days on Market

Townhome for Sale

$424,000

3 bd · 3 ba · 1,700 sqft

7435 RIPPLEPOINTE WAY, WINDERMERE, FL 34786

12744 LANGSTAFF DRIVE, WINDERMERE, FL 34786
9 Days on Market

Townhome for Sale

$420,000

3 bd · 3 ba · 1,369 sqft

12744 LANGSTAFF DRIVE, WINDERMERE, FL 34786

12405 CRUXBURY DRIVE, WINDERMERE, FL 34786
10 Days on Market

Townhome for Sale

$415,000

2 bd · 3 ba · 1,429 sqft

12405 CRUXBURY DRIVE, WINDERMERE, FL 34786

13366 ABUELA ALLEY, WINDERMERE, FL 34786
185 Days on Market

Townhome for Sale

$410,000

3 bd · 3 ba · 1,589 sqft

13366 ABUELA ALLEY, WINDERMERE, FL 34786

8218 MYSTIC VIEW WAY # 2801, WINDERMERE, FL 34786
30 Days on Market

Condo for Sale

$409,975

3 bd · 3 ba · 1,840 sqft

8218 MYSTIC VIEW WAY # 2801, WINDERMERE, FL 34786

5579 SOMERSBY ROAD, WINDERMERE, FL 34786
Newly Listed

Townhome for Sale

$395,000

3 bd · 3 ba · 1,579 sqft

5579 SOMERSBY ROAD, WINDERMERE, FL 34786

Talk to a local agent

Looking at Windermere Homes for Sale under $500K?

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
Matthew Gromadzki
Real Estate Broker
(786) 370-8570
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Live MLS inventory in Windermere, updated continuously. Florida Lux Real Estate currently tracks 36 active listings here. MLS inventory updated October 14, 2026.

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