321 total properties
Did you mean the neighborhood Windermere?
View 5526 MARLEON DRIVE Windermere, FL MLS# S5156252
  • Recently Listed with Virtual Tour
1 of 98
$2,500,000
5

Beds

3.2

Baths

4,661

Sq.Ft.

5526 MARLEON DRIVE

Windermere, FL

Courtesy of SERHANT
View 13325 LUSH LIME ALLEY Windermere, FL MLS# TB8544045
  • Recently Listed with Virtual Tour
1 of 22
$641,681
3

Beds

2.1

Baths

1,714

Sq.Ft.

13325 LUSH LIME ALLEY

Windermere, FL

View 13503 LAKE CAWOOD DRIVE Windermere, FL MLS# TB8542427
  • Recently Listed with Virtual Tour
1 of 34
$1,500,000
5

Beds

6.1

Baths

5,312

Sq.Ft.

13503 LAKE CAWOOD DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 12989 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6437718
  • Recently Listed with Virtual Tour
1 of 33
$1,159,000
4

Beds

3.1

Baths

2,665

Sq.Ft.

12989 WESTSIDE VILLAGE LOOP

Windermere, FL

View 2540 HEMPEL COVE CT Windermere, FL MLS# O6436594
  • Recently Listed with Virtual Tour
1 of 70
$1,399,900
5

Beds

3.0

Baths

3,356

Sq.Ft.

2540 HEMPEL COVE CT

Windermere, FL

View 14077 ANCILLA BOULEVARD Windermere, FL MLS# O6437694
  • Recently Listed with Virtual Tour
1 of 70
$399,000
3

Beds

2.1

Baths

1,651

Sq.Ft.

14077 ANCILLA BOULEVARD

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6438618
$3,189,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 8641 BROOKVALE DRIVE Windermere, FL MLS# O6433201
  • Recently Listed with Virtual Tour
1 of 23
$410,000
3

Beds

2.1

Baths

1,526

Sq.Ft.

8641 BROOKVALE DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 930 EAST BOULEVARD Windermere, FL MLS# O6437093
  • Recently Listed with Virtual Tour
1 of 70
$1,895,000
4

Beds

4.1

Baths

2,868

Sq.Ft.

930 EAST BOULEVARD

Windermere, FL

View 4844 FLINT ROAD Windermere, FL MLS# O6436938
  • Recently Listed with Virtual Tour
1 of 20
OPEN HOUSE: Sunday 9/13 1:00 PM - 4:00 PM
$529,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4844 FLINT ROAD

Windermere, FL

View 6309 EARTHGOLD DRIVE Windermere, FL MLS# O6436644
  • Recently Listed with Virtual Tour
1 of 30
$880,000
4

Beds

2.1

Baths

2,648

Sq.Ft.

6309 EARTHGOLD DRIVE

Windermere, FL

Courtesy of REALTY HUB
View 13321 LUSH LIME ALLEY Windermere, FL MLS# TB8542700
  • Recently Listed with Virtual Tour
1 of 21
$556,256
3

Beds

2.1

Baths

1,649

Sq.Ft.

13321 LUSH LIME ALLEY

Windermere, FL

View 4302 ISABELLA CIR Windermere, FL MLS# O6436735
  • Recently Listed with Virtual Tour
1 of 90
$3,700,000
5

Beds

6.1

Baths

5,362

Sq.Ft.

4302 ISABELLA CIR

Windermere, FL

View 13239 JERVEY STREET Windermere, FL MLS# O6436893
  • Recently Listed with Virtual Tour
1 of 56
$710,999
4

Beds

3.1

Baths

2,745

Sq.Ft.

13239 JERVEY STREET

Windermere, FL

Courtesy of LPT REALTY, LLC
View 7430 BENTONSHIRE AVENUE Windermere, FL MLS# O6436022
  • Recently Listed with Virtual Tour
1 of 59
OPEN HOUSE: Sunday 9/13 12:00 PM - 3:00 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
  • Recently Listed with Virtual Tour
1 of 57
$445,000
3

Beds

2.1

Baths

1,727

Sq.Ft.

11734 WATER RUN ALLEY

Windermere, FL

View 9043 HORIZON POINTE TRAIL Windermere, FL MLS# O6436017
  • Recently Listed with Virtual Tour
1 of 53
$870,000
4

Beds

3.0

Baths

3,746

Sq.Ft.

9043 HORIZON POINTE TRAIL

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 8168 BOAT HOOK LOOP 303 Windermere, FL MLS# O6435857
  • Recently Listed with Virtual Tour
1 of 20
$320,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8168 BOAT HOOK LOOP 303

Windermere, FL

View 1243 DINGENS AVENUE Windermere, FL MLS# O6435494
  • Recently Listed with Virtual Tour
1 of 55
$990,000
4

Beds

3.0

Baths

2,728

Sq.Ft.

1243 DINGENS AVENUE

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

321

Estimated median home price

$975,000
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 - 400K25
$400K - 500K34
$500K - 600K28
$600K - 700K32
$700K - 800K21
$800K - 900K11
$900K - 1M14
$1M - Max153

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family241
Townhouse51
Condo9
Commercial1
Rental86
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 9/13/2026)

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 9/13/2026.