109 total properties
Did you mean the neighborhood Windermere?
View 6871 HELMSLEY CIRCLE Windermere, FL MLS# O6387593
$554,000
3

Beds

2.0

Baths

1,772

Sq.Ft.

6871 HELMSLEY CIRCLE

Windermere, FL

Courtesy of SOUTH KEY REALTY LLC
View 13013 OVERSTREET ROAD Windermere, FL MLS# O6380917
$649,994
4

Beds

2.1

Baths

2,053

Sq.Ft.

13013 OVERSTREET ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 9319 WOODBREEZE BOULEVARD Windermere, FL MLS# O6384930
$554,555
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 6390 SOUTHBRIDGE STREET Windermere, FL MLS# O6385153
  • Recently Listed with Virtual Tour
1 of 34
$395,000
4

Beds

2.1

Baths

1,632

Sq.Ft.

6390 SOUTHBRIDGE STREET

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 8552 POWDER RIDGE TRAIL Windermere, FL MLS# S5144276
$680,000
5

Beds

3.1

Baths

2,612

Sq.Ft.

8552 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
$455,000
3

Beds

2.1

Baths

2,002

Sq.Ft.

13733 BRESSLER ALLEY

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 6673 DUNCASTER STREET Windermere, FL MLS# O6378820
$530,000
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
$649,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 8650 ABBOTSBURY DRIVE Windermere, FL MLS# O6376488
$575,000
4

Beds

3.1

Baths

2,628

Sq.Ft.

8650 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of THE AGENCY FL
View 13366 ABUELA ALLEY Windermere, FL MLS# O6374298
$430,000
3

Beds

2.1

Baths

1,589

Sq.Ft.

13366 ABUELA ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 8180 BOAT HOOK LOOP 108/301 Windermere, FL MLS# TB8465266
$322,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8180 BOAT HOOK LOOP 108/301

Windermere, FL

Courtesy of EXP REALTY LLC
View 12305 VIA DERNA PLACE Windermere, FL MLS# O6374964
$465,000
3

Beds

3.0

Baths

1,891

Sq.Ft.

12305 VIA DERNA PLACE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 13232 LONGACRE DRIVE Windermere, FL MLS# O6372809
$689,000
5

Beds

3.0

Baths

2,511

Sq.Ft.

13232 LONGACRE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13339 ROSKIN LANE Windermere, FL MLS# S5141148
  • Virtual Tour
1 of 59
$680,000
4

Beds

2.1

Baths

2,947

Sq.Ft.

13339 ROSKIN LANE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 6442 GOLDEN DEWDROP TRAIL Windermere, FL MLS# G5106279
$575,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 8225 BRYCE CANYON AVENUE Windermere, FL MLS# O6371960
$560,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

8225 BRYCE CANYON AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6362685
$458,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of YELLOW ROCK REALTY CORP
View 6799 HELMSLEY CIRCLE Windermere, FL MLS# O6361417
$658,000
4

Beds

3.1

Baths

2,615

Sq.Ft.

6799 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 2 CHASE ROAD Windermere, FL MLS# O6345181
$575,000
Studio

Beds

0.0

Baths

2 CHASE ROAD

Windermere, FL

Courtesy of REAL BROKER, LLC
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
$408,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC

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

357

Estimated median home price

$1,190,000
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 - 300K1
$300K - 400K22
$400K - 500K31
$500K - 600K33
$600K - 700K25
$700K - 800K17
$800K - 900K18
$900K - 1M14
$1M - Max196

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family291
Townhouse44
Condo7
Commercial1
Rental91
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/4/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 6/5/2026.