59 total properties
Did you mean the neighborhood Windermere?
View 7924 BROFIELD AVENUE Windermere, FL MLS# S5146185
$650,000
3

Beds

2.1

Baths

1,709

Sq.Ft.

7924 BROFIELD AVENUE

Windermere, FL

Courtesy of ALTIS REALTY
View 7208 TATTANT BOULEVARD Windermere, FL MLS# O6389785
$599,000
4

Beds

2.0

Baths

2,215

Sq.Ft.

7208 TATTANT BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 6573 HELMSLEY CIRCLE Windermere, FL MLS# S5145061
$639,900
4

Beds

3.1

Baths

2,664

Sq.Ft.

6573 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WATSON REALTY CORP.
The time to sell is now! THE TIME TO SELL IS NOW!
View 7264 BACKWOODS TRAIL Windermere, FL MLS# O6387913
$650,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7264 BACKWOODS TRAIL

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 13118 SUNKISS LOOP Windermere, FL MLS# O6385211
$579,000
4

Beds

2.1

Baths

2,547

Sq.Ft.

13118 SUNKISS LOOP

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
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
$669,994
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
View 13243 CHARFIELD STREET Windermere, FL MLS# O6385405
$699,000
4

Beds

3.1

Baths

2,794

Sq.Ft.

13243 CHARFIELD STREET

Windermere, FL

Courtesy of REAL BROKER, LLC
View 8552 POWDER RIDGE TRAIL Windermere, FL MLS# S5144276
$680,000
4

Beds

2.1

Baths

2,612

Sq.Ft.

8552 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
$599,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
$560,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
$689,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA 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 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
$629,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6376756
$725,000
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of U S GLORY REALTY
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 11578 ASHLIN PARK BOULEVARD Windermere, FL MLS# O6373714
$619,900
5

Beds

3.1

Baths

2,396

Sq.Ft.

11578 ASHLIN PARK BOULEVARD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 11531 VICOLO LOOP Windermere, FL MLS# O6374016
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$600,000
4

Beds

2.0

Baths

2,280

Sq.Ft.

11531 VICOLO LOOP

Windermere, FL

Courtesy of THE ROSENBLOOM TEAM
View 8632 ABBOTSBURY DRIVE Windermere, FL MLS# O6374937
$609,999
4

Beds

3.1

Baths

2,720

Sq.Ft.

8632 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS

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

352

Estimated median home price

$1,116,995
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 - 400K20
$400K - 500K24
$500K - 600K38
$600K - 700K24
$700K - 800K24
$800K - 900K22
$900K - 1M16
$1M - Max183

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family295
Townhouse37
Condo7
Commercial1
Rental96
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/1/2026)

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 5/1/2026.