316 total properties
View 12840 CALDERDALE AVENUE Windermere, FL MLS# O6381937
$435,000
4

Beds

3.1

Baths

1,905

Sq.Ft.

12840 CALDERDALE AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
$469,999
3

Beds

2.1

Baths

2,002

Sq.Ft.

13733 BRESSLER ALLEY

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 6023 BLAKEFORD DR Windermere, FL MLS# O6381942
  • Virtual Tour
1 of 47
$1,525,000
5

Beds

3.0

Baths

3,013

Sq.Ft.

6023 BLAKEFORD DR

Windermere, FL

Courtesy of KEENE'S POINTE REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8767 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6379681
$870,000
5

Beds

3.1

Baths

3,724

Sq.Ft.

8767 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of KARDOSH REALTY
View 58 MAIN STREET Windermere, FL MLS# O6370886
  • Virtual Tour
1 of 52
$3,725,000
5

Beds

4.0

Baths

4,875

Sq.Ft.

58 MAIN STREET

Windermere, FL

Courtesy of LPT REALTY, LLC
View 6673 DUNCASTER STREET Windermere, FL MLS# O6378820
  • Recently Listed with Virtual Tour
1 of 48
$579,000
3

Beds

2.0

Baths

2,151

Sq.Ft.

6673 DUNCASTER STREET

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 6001 CAYMUS LOOP Windermere, FL MLS# O6379564
  • Virtual Tour
1 of 44
$1,599,000
5

Beds

5.0

Baths

3,520

Sq.Ft.

6001 CAYMUS LOOP

Windermere, FL

Courtesy of QUATTRO R E SOLUTIONS LLC
View 13734 LAKE CAWOOD DRIVE Windermere, FL MLS# G5107723
$1,620,000
4

Beds

3.1

Baths

4,437

Sq.Ft.

13734 LAKE CAWOOD DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
  • Virtual Tour
1 of 76
$749,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 7422 BENTONSHIRE AVENUE Windermere, FL MLS# O6380109
$349,000
2

Beds

2.1

Baths

1,360

Sq.Ft.

7422 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 3013 SEIGNEURY DRIVE Windermere, FL MLS# O6377087
  • Virtual Tour
1 of 62
$1,890,000
4

Beds

3.2

Baths

5,130

Sq.Ft.

3013 SEIGNEURY DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
$595,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6382 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 1134 KELSO BOULEVARD Windermere, FL MLS# O6378782
  • Virtual Tour
1 of 37
$1,590,000
2

Beds

2.0

Baths

2,044

Sq.Ft.

1134 KELSO BOULEVARD

Windermere, FL

Courtesy of REALTY AND COMPANY INT., LLC
View 2931 SUNBITTERN COURT Windermere, FL MLS# O6378100
  • Virtual Tour
1 of 56
$1,199,000
4

Beds

3.0

Baths

4,018

Sq.Ft.

2931 SUNBITTERN COURT

Windermere, FL

Courtesy of REVEL REALTY LLC
View 10870 BAYSHORE DRIVE Windermere, FL MLS# O6371471
  • Virtual Tour
1 of 60
$2,995,000
4

Beds

5.0

Baths

4,693

Sq.Ft.

10870 BAYSHORE DRIVE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 6248 LOUISE COVE DR Windermere, FL MLS# O6378223
$2,850,000
5

Beds

5.1

Baths

6,253

Sq.Ft.

6248 LOUISE COVE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 12779 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6377817
$1,274,000
5

Beds

3.1

Baths

3,689

Sq.Ft.

12779 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 8168 BOAT HOOK LOOP 207/714 Windermere, FL MLS# O6378432
$316,500
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 207/714

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 5538 W LAKE BUTLER ROAD Windermere, FL MLS# O6376859
$3,495,000
6

Beds

5.1

Baths

6,000

Sq.Ft.

5538 W LAKE BUTLER ROAD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5018 RIVER GEM AVENUE Windermere, FL MLS# TB8469061
$785,000
3

Beds

2.1

Baths

2,379

Sq.Ft.

5018 RIVER GEM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 3/16/2026.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 3/16/2026.