32 total properties
Did you mean the neighborhood Windermere?
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
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 8638 BROOKVALE DRIVE Windermere, FL MLS# O6360958
  • Recently Listed
1 of 4
$395,000
3

Beds

2.1

Baths

1,520

Sq.Ft.

8638 BROOKVALE DRIVE

Windermere, FL

Courtesy of AK GLOBAL REALTY LLC
View 7768 MOSER AVENUE Windermere, FL MLS# O6355727
$375,000
3

Beds

2.1

Baths

1,644

Sq.Ft.

7768 MOSER AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 12716 LANGSTAFF DRIVE Windermere, FL MLS# O6352910
$345,000
2

Beds

2.1

Baths

1,181

Sq.Ft.

12716 LANGSTAFF DRIVE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 7711 FAIRGROVE AVENUE Windermere, FL MLS# O6352360
$389,900
3

Beds

2.1

Baths

1,680

Sq.Ft.

7711 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VOSS REALTY INC
View 11818 WATER RUN ALLEY Windermere, FL MLS# O6353649
$410,000
3

Beds

2.1

Baths

1,588

Sq.Ft.

11818 WATER RUN ALLEY

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8179 MARITIME FLAG STREET 202/108 Windermere, FL MLS# S5136502
$327,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8179 MARITIME FLAG STREET 202/108

Windermere, FL

Courtesy of THE FIRM RE
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
$428,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 8180 BOAT HOOK LOOP 106/306 Windermere, FL MLS# O6353569
$324,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

8180 BOAT HOOK LOOP 106/306

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7628 BILLINGHAM STREET Windermere, FL MLS# O6343842
$398,000
3

Beds

2.1

Baths

1,480

Sq.Ft.

7628 BILLINGHAM STREET

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8259 MARITIME FLAG STREET 4 Windermere, FL MLS# O6329585
$330,000
3

Beds

2.1

Baths

1,460

Sq.Ft.

8259 MARITIME FLAG STREET 4

Windermere, FL

Courtesy of REAL BROKER, LLC
View 14155 ANCILLA BOULEVARD Windermere, FL MLS# O6327707
$399,000
3

Beds

2.1

Baths

1,629

Sq.Ft.

14155 ANCILLA BOULEVARD

Windermere, FL

Courtesy of COMPASS FLORIDA 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

290

Estimated median home price

$1,060,000
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 - Max150

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family230
Townhouse38
Condo9
Commercial1
Rental111
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/25/2025)

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 12/26/2025.