103 total properties
Did you mean the neighborhood Windermere?
View 6310 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6368983
  • Recently Listed with Virtual Tour
1 of 15
$525,000
3

Beds

2.1

Baths

1,977

Sq.Ft.

6310 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of JOY ESTATE ENTERPRISE INC
View 7418 BENTONSHIRE AVENUE Windermere, FL MLS# O6368156
  • Recently Listed with Virtual Tour
1 of 36
$330,000
2

Beds

2.1

Baths

1,228

Sq.Ft.

7418 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 6343 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6368529
  • Recently Listed with Virtual Tour
1 of 42
$339,775
2

Beds

2.0

Baths

1,068

Sq.Ft.

6343 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 4533 RIVER GEM AVENUE Windermere, FL MLS# O6369079
  • Recently Listed with Virtual Tour
1 of 40
$625,000
4

Beds

3.0

Baths

2,406

Sq.Ft.

4533 RIVER GEM AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 7777 MOSER AVENUE Windermere, FL MLS# O6367366
  • Virtual Tour
1 of 32
$399,000
3

Beds

2.1

Baths

1,670

Sq.Ft.

7777 MOSER AVENUE

Windermere, FL

Courtesy of CREEGAN GROUP
View 11565 MIZZON DRIVE 101/808 Windermere, FL MLS# O6366930
  • Recently Listed with Virtual Tour
1 of 26
$315,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

11565 MIZZON DRIVE 101/808

Windermere, FL

Courtesy of HOMEVEST REALTY
View 8180 BOAT HOOK LOOP 321 Windermere, FL MLS# O6367323
  • Recently Listed with Virtual Tour
1 of 26
$325,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8180 BOAT HOOK LOOP 321

Windermere, FL

Courtesy of DOUG STEWART REALTY, INC
View 825 OAKDALE STREET Windermere, FL MLS# O6364501
$750,000
3

Beds

2.0

Baths

1,664

Sq.Ft.

825 OAKDALE STREET

Windermere, FL

Courtesy of EXP REALTY LLC
View 7482 BENTONSHIRE AVENUE Windermere, FL MLS# O6366524
  • Recently Listed with Virtual Tour
1 of 21
$399,900
3

Beds

2.1

Baths

1,428

Sq.Ft.

7482 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 13907 ANCILLA BOULEVARD Windermere, FL MLS# O6365074
$360,000
2

Beds

2.0

Baths

1,155

Sq.Ft.

13907 ANCILLA BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 11562 AMIDSHIP LANE 207 Windermere, FL MLS# O6365492
  • Recently Listed with Virtual Tour
1 of 25
$319,900
3

Beds

2.0

Baths

1,455

Sq.Ft.

11562 AMIDSHIP LANE 207

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 7167 BEEK STREET Windermere, FL MLS# O6364480
  • Recently Listed
1 of 69
$759,900
4

Beds

3.0

Baths

2,425

Sq.Ft.

7167 BEEK STREET

Windermere, FL

Courtesy of RE/MAX CENTRAL REALTY
View 13808 ANCILLA BOULEVARD Windermere, FL MLS# S5139822
$414,999
3

Beds

2.1

Baths

1,461

Sq.Ft.

13808 ANCILLA BOULEVARD

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 12307 LANGSTAFF DRIVE Windermere, FL MLS# O6364588
$369,999
3

Beds

2.1

Baths

1,520

Sq.Ft.

12307 LANGSTAFF DRIVE

Windermere, FL

Courtesy of HOGAN REALTY GROUP INC
View 13833 ANCILLA BOULEVARD Windermere, FL MLS# O6364332
$355,000
2

Beds

2.0

Baths

1,155

Sq.Ft.

13833 ANCILLA BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 13290 ORANGE ISLE DRIVE Windermere, FL MLS# O6365010
  • Recently Listed with Virtual Tour
1 of 26
$650,000
3

Beds

2.0

Baths

2,146

Sq.Ft.

13290 ORANGE ISLE DRIVE

Windermere, FL

Courtesy of PREMIUM REALTY GROUP USA
View 13927 BLUEBIRD POND ROAD Windermere, FL MLS# O6363255
$535,000
4

Beds

3.0

Baths

2,345

Sq.Ft.

13927 BLUEBIRD POND ROAD

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
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 7028 VENTNOR DRIVE Windermere, FL MLS# O6363663
$515,000
4

Beds

3.0

Baths

1,980

Sq.Ft.

7028 VENTNOR DRIVE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC

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

$1,045,000
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 - 300K0
$300K - 400K25
$400K - 500K25
$500K - 600K15
$600K - 700K21
$700K - 800K17
$800K - 900K20
$900K - 1M17
$1M - Max149

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family229
Townhouse38
Condo9
Commercial1
Rental111
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/24/2025)

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 12/25/2025.