85 total properties
Did you mean the neighborhood Windermere?
View 12661 CALDERDALE AVENUE Windermere, FL MLS# O6364859
$495,000
3

Beds

2.0

Baths

1,696

Sq.Ft.

12661 CALDERDALE AVENUE

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 13757 BRESSLER ALLEY Windermere, FL MLS# O6332021
  • Virtual Tour
1 of 42
$474,900
3

Beds

2.1

Baths

2,113

Sq.Ft.

13757 BRESSLER ALLEY

Windermere, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
View 13333 GORGONA ISLE DRIVE Windermere, FL MLS# O6330691
$460,000
3

Beds

2.1

Baths

1,779

Sq.Ft.

13333 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 13752 BRESSLER ALLEY Windermere, FL MLS# O6358878
  • Virtual Tour
1 of 30
$460,000
3

Beds

2.1

Baths

1,976

Sq.Ft.

13752 BRESSLER ALLEY

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 8937 MATRIARCA ALLEY Windermere, FL MLS# O6347945
  • New Construction with Virtual Tour
1 of 17
$459,000
3

Beds

2.1

Baths

1,730

Sq.Ft.

8937 MATRIARCA ALLEY

Windermere, FL

Courtesy of SANCTUM REALTY PROFESSIONALS LLC
View 11692 WATER RUN ALLEY Windermere, FL MLS# O6358611
  • Virtual Tour
1 of 34
$459,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

11692 WATER RUN ALLEY

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6362685
  • Virtual Tour
1 of 57
$459,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of YELLOW ROCK REALTY CORP
View 13775 BRESSLER ALLEY Windermere, FL MLS# O6342957
  • Virtual Tour
1 of 40
$455,000
3

Beds

2.1

Baths

2,001

Sq.Ft.

13775 BRESSLER ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 5844 SOTER LANE Windermere, FL MLS# O6366829
  • Recently Listed with Virtual Tour
1 of 39
$449,000
3

Beds

2.1

Baths

1,976

Sq.Ft.

5844 SOTER LANE

Windermere, FL

Courtesy of SERHANT
View 7411 RIPPLEPOINTE WAY Windermere, FL MLS# O6360114
  • Virtual Tour
1 of 24
$440,000
3

Beds

2.1

Baths

1,948

Sq.Ft.

7411 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 7625 SUTHERTON LANE Windermere, FL MLS# O6363486
$439,000
3

Beds

2.1

Baths

1,565

Sq.Ft.

7625 SUTHERTON LANE

Windermere, FL

Courtesy of SOLD BY SIX REALTY, LLC
View 8237 SERENITY SPRING DRIVE 2605 Windermere, FL MLS# O6280344
$432,000
4

Beds

2.1

Baths

2,028

Sq.Ft.

8237 SERENITY SPRING DRIVE 2605

Windermere, FL

Courtesy of INT'L PROFESSIONAL REALTY INC
View 12930 VENNETTA WAY Windermere, FL MLS# O6301208
  • Virtual Tour
1 of 38
$429,900
3

Beds

2.1

Baths

1,644

Sq.Ft.

12930 VENNETTA WAY

Windermere, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 11637 Water Run ALLEY Windermere, FL MLS# O6194326
$429,000
3

Beds

2.1

Baths

1,466

Sq.Ft.

11637 Water Run ALLEY

Windermere, FL

Courtesy of LOKATION
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
  • Virtual Tour
1 of 18
$428,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 13808 ANCILLA BOULEVARD Windermere, FL MLS# S5139822
  • Adult Community
1 of 40
$414,999
3

Beds

2.1

Baths

1,461

Sq.Ft.

13808 ANCILLA BOULEVARD

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 12744 LANGSTAFF DRIVE Windermere, FL MLS# O6322751
  • Virtual Tour
1 of 20
$410,000
3

Beds

2.1

Baths

1,369

Sq.Ft.

12744 LANGSTAFF DRIVE

Windermere, FL

Courtesy of PROPERTY WAREHOUSES OF AMERICA
View 11818 WATER RUN ALLEY Windermere, FL MLS# O6353649
  • Virtual Tour
1 of 32
$410,000
3

Beds

2.1

Baths

1,588

Sq.Ft.

11818 WATER RUN ALLEY

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 11686 WATER RUN ALLEY Windermere, FL MLS# O6321724
  • Virtual Tour
1 of 24
$409,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11686 WATER RUN ALLEY

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 8625 COVENTRY PARK WAY Windermere, FL MLS# O6325457
$401,990
3

Beds

2.1

Baths

1,554

Sq.Ft.

8625 COVENTRY PARK WAY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL 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

289

Estimated median home price

$1,075,000
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 0
$300K - 400K 25
$400K - 500K 23
$500K - 600K 16
$600K - 700K 21
$700K - 800K 17
$800K - 900K 20
$900K - 1M 17
$1M - Max 150

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 229
Townhouse 38
Condo 9
Commercial 1
Rental 112
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/27/2025)

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 12/28/2025.