108 total properties
Did you mean the neighborhood Windermere?
View 11434 JASPER KAY TERRACE 106 Windermere, FL MLS# S5150874
$320,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

11434 JASPER KAY TERRACE 106

Windermere, FL

Courtesy of NUMBER 1 BROKER, LLC
View 11822 SILVERLAKE PARK DRIVE Windermere, FL MLS# O6409301
  • Recently Listed with Virtual Tour
1 of 29
$495,000
3

Beds

2.1

Baths

1,829

Sq.Ft.

11822 SILVERLAKE PARK DRIVE

Windermere, FL

Courtesy of REDFIN CORPORATION
View 13019 LANGSTAFF DRIVE Windermere, FL MLS# O6411551
  • Recently Listed with Virtual Tour
1 of 52
$360,000
2

Beds

2.1

Baths

1,375

Sq.Ft.

13019 LANGSTAFF DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 12319 CRUXBURY DRIVE Windermere, FL MLS# O6411226
  • Recently Listed with Virtual Tour
1 of 58
$405,000
3

Beds

2.1

Baths

1,429

Sq.Ft.

12319 CRUXBURY DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13450 SUNKISS LOOP Windermere, FL MLS# O6407409
  • Recently Listed
1 of 16
$574,900
5

Beds

2.1

Baths

2,272

Sq.Ft.

13450 SUNKISS LOOP

Windermere, FL

Courtesy of ENTERA REALTY LLC
View 11951 VERMILLION AVENUE Windermere, FL MLS# O6411413
  • Recently Listed with Virtual Tour
1 of 52
$459,000
3

Beds

2.1

Baths

1,539

Sq.Ft.

11951 VERMILLION AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12633 HADDON DRIVE Windermere, FL MLS# O6411199
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Sunday 5/31 1:00 PM - 3:00 PM
$650,000
5

Beds

3.1

Baths

3,000

Sq.Ft.

12633 HADDON DRIVE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 12555 CRUXBURY DRIVE Windermere, FL MLS# O6410796
  • Recently Listed with Virtual Tour
1 of 41
$350,000
2

Beds

2.1

Baths

1,211

Sq.Ft.

12555 CRUXBURY DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 13730 CALERA ALLEY Windermere, FL MLS# O6410129
  • Recently Listed with Virtual Tour
1 of 58
$465,000
4

Beds

2.1

Baths

2,091

Sq.Ft.

13730 CALERA ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 9376 WOODBREEZE BOULEVARD Windermere, FL MLS# O6411270
  • Recently Listed with Virtual Tour
1 of 42
$675,000
4

Beds

2.1

Baths

2,026

Sq.Ft.

9376 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13732 SUMMER HARBOR COURT Windermere, FL MLS# O6410454
  • Recently Listed with Virtual Tour
1 of 20
$599,000
4

Beds

2.1

Baths

2,236

Sq.Ft.

13732 SUMMER HARBOR COURT

Windermere, FL

Courtesy of SANCHEZ PROPERTIES GROUP LLC
View 11401 EVESHAM DRIVE Windermere, FL MLS# O6410182
  • Recently Listed with Virtual Tour
1 of 47
$440,000
3

Beds

2.1

Baths

1,847

Sq.Ft.

11401 EVESHAM DRIVE

Windermere, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 7867 BERKSHIRE OAK ALLEY Windermere, FL MLS# S5149947
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Saturday 5/30 10:00 AM - 4:00 PM
$539,000
4

Beds

2.1

Baths

2,221

Sq.Ft.

7867 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
View 14005 SPARKLING COVE LANE Windermere, FL MLS# O6409827
  • Recently Listed with Virtual Tour
1 of 56
$375,000
3

Beds

2.1

Baths

1,647

Sq.Ft.

14005 SPARKLING COVE LANE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 14442 DESERT HAVEN STREET 4305 Windermere, FL MLS# O6410152
  • Recently Listed with Virtual Tour
1 of 19
$359,900
3

Beds

2.1

Baths

1,534

Sq.Ft.

14442 DESERT HAVEN STREET 4305

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 8360 VIVARO ISLE WAY Windermere, FL MLS# S5150324
  • Virtual Tour
1 of 11
$690,000
4

Beds

3.0

Baths

2,224

Sq.Ft.

8360 VIVARO ISLE WAY

Windermere, FL

Courtesy of MD3 HOMES LLC
View 8180 BOAT HOOK LOOP 109 Windermere, FL MLS# S5150297
  • Recently Listed with Virtual Tour
1 of 19
$299,500
2

Beds

2.0

Baths

1,161

Sq.Ft.

8180 BOAT HOOK LOOP 109

Windermere, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 811 MAIN STREET Windermere, FL MLS# O6409463
  • Recently Listed with Virtual Tour
1 of 33
$649,999
2

Beds

1.1

Baths

1,398

Sq.Ft.

811 MAIN STREET

Windermere, FL

Courtesy of CAMERON REALTY GROUP LLC
View 6528 HELMSLEY CIRCLE Windermere, FL MLS# O6408661
  • Virtual Tour
1 of 40
$325,000
2

Beds

2.1

Baths

1,411

Sq.Ft.

6528 HELMSLEY CIRCLE

Windermere, FL

Courtesy of NEW HEIGHTS REALTY GROUP
View 5225 LEMON TWIST LANE Windermere, FL MLS# O6406747
  • Virtual Tour
1 of 36
$499,900
3

Beds

2.0

Baths

1,700

Sq.Ft.

5225 LEMON TWIST LANE

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

349

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

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 1
$300K - 400K 21
$400K - 500K 28
$500K - 600K 32
$600K - 700K 24
$700K - 800K 20
$800K - 900K 19
$900K - 1M 16
$1M - Max 188

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 286
Townhouse 42
Condo 6
Commercial 1
Rental 99
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/29/2026)

Information deemed reliable but not guaranteed.

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 5/30/2026.