71 total properties
Did you mean the neighborhood Windermere?
View 12679 CALDERDALE AVENUE Windermere, FL MLS# O6442555
  • Recently Listed with Virtual Tour
1 of 28
$520,000
3

Beds

2.0

Baths

1,681

Sq.Ft.

12679 CALDERDALE AVENUE

Windermere, FL

Courtesy of NEWKEY REAL ESTATE LLC
View 929 LASCALA DRIVE Windermere, FL MLS# O6435895
  • Recently Listed with Virtual Tour
1 of 40
$349,900
3

Beds

2.0

Baths

1,852

Sq.Ft.

929 LASCALA DRIVE

Windermere, FL

View 8608 BROOKVALE DRIVE Windermere, FL MLS# S5157627
  • Recently Listed with Virtual Tour
1 of 46
$379,900
3

Beds

2.1

Baths

1,480

Sq.Ft.

8608 BROOKVALE DRIVE

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View DINGENS AVENUE Windermere, FL MLS# O6441380
  • Virtual Tour
1 of 23
$500,000
Studio

Beds

0.0

Baths

DINGENS AVENUE

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6441184
  • Recently Listed with Virtual Tour
1 of 53
$449,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of KARDOSH REALTY
View 5426 Kumquat Loop Windermere, FL MLS# B26074013
$400,000
2

Beds

2.0

Baths

1,155

Sq.Ft.

5426 Kumquat Loop

Windermere, FL

View 8156 BOAT HOOK LOOP 623 Windermere, FL MLS# O6439822
  • Recently Listed with Virtual Tour
1 of 20
$327,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

8156 BOAT HOOK LOOP 623

Windermere, FL

View 12417 CRUXBURY DRIVE Windermere, FL MLS# O6439656
  • Recently Listed with Virtual Tour
1 of 60
$360,000
2

Beds

2.1

Baths

1,311

Sq.Ft.

12417 CRUXBURY DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13730 LENSDALE LANE Windermere, FL MLS# O6439354
$375,000
4

Beds

2.1

Baths

1,640

Sq.Ft.

13730 LENSDALE LANE

Windermere, FL

View 9764 GOTHA ROAD Windermere, FL MLS# O6439109
  • Recently Listed
1 of 16
$450,000
2

Beds

1.0

Baths

1,216

Sq.Ft.

9764 GOTHA ROAD

Windermere, FL

View 13424 HOPKINTON COURT Windermere, FL MLS# O6438808
  • Recently Listed with Virtual Tour
1 of 38
$500,000
4

Beds

2.0

Baths

2,190

Sq.Ft.

13424 HOPKINTON COURT

Windermere, FL

View 13048 GARRIDAN AVENUE Windermere, FL MLS# O6437967
  • Recently Listed with Virtual Tour
1 of 24
$445,000
3

Beds

2.1

Baths

1,748

Sq.Ft.

13048 GARRIDAN AVENUE

Windermere, FL

View 14077 ANCILLA BOULEVARD Windermere, FL MLS# O6437694
$399,000
3

Beds

2.1

Baths

1,651

Sq.Ft.

14077 ANCILLA BOULEVARD

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 8641 BROOKVALE DRIVE Windermere, FL MLS# O6433201
$410,000
3

Beds

2.1

Baths

1,526

Sq.Ft.

8641 BROOKVALE DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 4844 FLINT ROAD Windermere, FL MLS# O6436938
  • Recently Listed with Virtual Tour
1 of 20
$519,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4844 FLINT ROAD

Windermere, FL

View 7430 BENTONSHIRE AVENUE Windermere, FL MLS# O6436022
  • Virtual Tour
1 of 59
OPEN HOUSE: Saturday 9/19 11:00 AM - 2:00 PM
$354,900
2

Beds

2.1

Baths

1,412

Sq.Ft.

7430 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of EXP REALTY LLC
View 11734 WATER RUN ALLEY Windermere, FL MLS# S5156211
$445,000
3

Beds

2.1

Baths

1,727

Sq.Ft.

11734 WATER RUN ALLEY

Windermere, FL

View 8168 BOAT HOOK LOOP 303 Windermere, FL MLS# O6435857
$320,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8168 BOAT HOOK LOOP 303

Windermere, FL

View PARK RIDGE GOTHA ROAD Windermere, FL MLS# S5156135
$200,000
Studio

Beds

0.0

Baths

PARK RIDGE GOTHA ROAD

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8860 HERENCIA ALLEY Windermere, FL MLS# O6433569
$409,900
3

Beds

2.1

Baths

1,547

Sq.Ft.

8860 HERENCIA ALLEY

Windermere, FL

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

320

Estimated median home price

$935,000
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 - 200K1
$200K - 300K2
$300K - 400K27
$400K - 500K33
$500K - 600K28
$600K - 700K35
$700K - 800K21
$800K - 900K10
$900K - 1M12
$1M - Max151

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family239
Townhouse52
Condo9
Commercial1
Rental88
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 9/17/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective 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 9/18/2026.