157 total properties
Did you mean the neighborhood Windermere?
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
$625,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 17520 BLACK RAIL STREET Windermere, FL MLS# O6384223
$777,000
4

Beds

2.0

Baths

2,380

Sq.Ft.

17520 BLACK RAIL STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 6990 SMITHSHIRE LANE Windermere, FL MLS# O6380372
$675,000
4

Beds

3.1

Baths

2,986

Sq.Ft.

6990 SMITHSHIRE LANE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 8324 VIVARO ISLE WAY Windermere, FL MLS# O6382641
$825,000
6

Beds

4.0

Baths

4,176

Sq.Ft.

8324 VIVARO ISLE WAY

Windermere, FL

Courtesy of AGENT GROUP REALTY
View 11835 GOLD CREEK TRAIL Windermere, FL MLS# O6382068
$900,000
4

Beds

4.1

Baths

3,119

Sq.Ft.

11835 GOLD CREEK TRAIL

Windermere, FL

Courtesy of BB GROUP REALTY CORP
View 11434 JASPER KAY TERRACE 1120 Windermere, FL MLS# O6382035
$315,000
3

Beds

2.0

Baths

1,332

Sq.Ft.

11434 JASPER KAY TERRACE 1120

Windermere, FL

Courtesy of REALTY ONE GROUP MVP
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
$580,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
View 9237 MCDAVID COURT Windermere, FL MLS# O6382243
$798,000
4

Beds

2.1

Baths

2,269

Sq.Ft.

9237 MCDAVID COURT

Windermere, FL

Courtesy of VINTAGE REALTY GROUP LLC
View 13712 SUMMERPORT VILLAGE PARKWAY Windermere, FL MLS# S5143431
$444,900
3

Beds

2.1

Baths

1,997

Sq.Ft.

13712 SUMMERPORT VILLAGE PARKWAY

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 9257 OUTLOOK ROCK TRAIL Windermere, FL MLS# S5143447
$899,990
5

Beds

4.1

Baths

3,619

Sq.Ft.

9257 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of PRIMUS CRE GROUP
View 13302 ROSKIN LANE Windermere, FL MLS# O6380701
  • Virtual Tour
1 of 46
$899,900
4

Beds

3.1

Baths

3,424

Sq.Ft.

13302 ROSKIN LANE

Windermere, FL

Courtesy of RATIO REAL ESTATE, LLC
View 7123 CALM COVE COURT Windermere, FL MLS# O6380782
$814,000
4

Beds

3.1

Baths

3,044

Sq.Ft.

7123 CALM COVE COURT

Windermere, FL

Courtesy of RE/MAX PRIME 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 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 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 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
$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 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 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

About Windermere

"Among the lakes" is the phrase that the town of Windermere has chosen for its description, and aptly so.  Almost completely surrounded by water, Windermere is a lovely small town that will always be limited in population growth by available land.  Lake Butler is the largest body of water in the region, which is often referred to as the "Butler chain of lakes."  Situated in southeast Orange County, the residential villages and homes throughout the lake area are as beautiful as the backdrop of scenery they enjoy.  Some multi-million dollar lakefront mansions combine with more modest but often luxurious homes in a variety of architectural styles.  The Islesworth Golf & Country Club in Windermere rivals the lush fairways of highly acclaimed Bay Hill for sheer bayside splendor.  Also located in this small town is a fully accredited independent school for students in pre-kindergarten through eighth grade called Buena Vista Academy.  While the residents of Windermere can enjoy the exclusive resort setting and serenity of their community, the first-rate cultural, educational, and healthcare advantages of Orlando remain close to home. 

Listings in Windermere, FL

315

Estimated median home price

$1,029,990
Windermere FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Windermere, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Windermere, FL.

Homes for Sale by Price in Windermere, FL

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K16
$400K - 500K26
$500K - 600K32
$600K - 700K22
$700K - 800K24
$800K - 900K20
$900K - 1M17
$1M - Max158

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family260
Townhouse38
Condo3
Commercial1
Rental97
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/16/2026)

Information deemed reliable but not guaranteed.

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 3/17/2026.