255 total properties
Did you mean the neighborhood Windermere?
View 706 OAKDALE STREET Windermere, FL MLS# O6439213
$850,000
3

Beds

3.0

Baths

2,048

Sq.Ft.

706 OAKDALE STREET

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 8104 JAILENE DRIVE Windermere, FL MLS# O6437963
$759,000
4

Beds

3.1

Baths

2,886

Sq.Ft.

8104 JAILENE DRIVE

Windermere, FL

View 5379 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6438449
$2,900,000
4

Beds

3.1

Baths

3,872

Sq.Ft.

5379 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 12909 CRAGSIDE LANE Windermere, FL MLS# S5157040
$639,500
4

Beds

2.1

Baths

2,460

Sq.Ft.

12909 CRAGSIDE LANE

Windermere, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 13424 HOPKINTON COURT Windermere, FL MLS# O6438808
$500,000
4

Beds

2.0

Baths

2,190

Sq.Ft.

13424 HOPKINTON COURT

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 5526 MARLEON DRIVE Windermere, FL MLS# S5156252
$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
  • New Construction with Virtual Tour
1 of 22
$645,178
3

Beds

2.1

Baths

1,714

Sq.Ft.

13325 LUSH LIME ALLEY

Windermere, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 13503 LAKE CAWOOD DRIVE Windermere, FL MLS# TB8542427
$1,500,000
5

Beds

6.1

Baths

5,312

Sq.Ft.

13503 LAKE CAWOOD DRIVE

Windermere, FL

View 13048 GARRIDAN AVENUE Windermere, FL MLS# O6437967
$445,000
3

Beds

2.1

Baths

1,748

Sq.Ft.

13048 GARRIDAN AVENUE

Windermere, FL

View 9155 OUTLOOK ROCK TRAIL Windermere, FL MLS# O6438208
$795,000
5

Beds

4.1

Baths

3,566

Sq.Ft.

9155 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of SERHANT
View 12989 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6437718
$1,159,000
4

Beds

3.1

Baths

2,665

Sq.Ft.

12989 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 2540 HEMPEL COVE CT Windermere, FL MLS# O6436594
$1,349,900
5

Beds

3.0

Baths

3,356

Sq.Ft.

2540 HEMPEL COVE CT

Windermere, FL

Courtesy of ALIGN REAL ESTATE LLC
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 101 LEE STREET Windermere, FL MLS# O6437573
  • Virtual Tour
1 of 63
$1,395,000
5

Beds

4.0

Baths

4,186

Sq.Ft.

101 LEE STREET

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
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 930 EAST BOULEVARD Windermere, FL MLS# O6437093
$1,895,000
4

Beds

4.1

Baths

2,868

Sq.Ft.

930 EAST BOULEVARD

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 4844 FLINT ROAD Windermere, FL MLS# O6436938
  • Virtual Tour
1 of 20
$519,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4844 FLINT ROAD

Windermere, FL

View 6309 EARTHGOLD DRIVE Windermere, FL MLS# O6436644
$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
  • New Construction with Virtual Tour
1 of 21
$556,256
3

Beds

2.1

Baths

1,649

Sq.Ft.

13321 LUSH LIME ALLEY

Windermere, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 13239 JERVEY STREET Windermere, FL MLS# O6436893
$699,990
4

Beds

3.1

Baths

2,745

Sq.Ft.

13239 JERVEY STREET

Windermere, FL

Courtesy of LPT REALTY, 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

324

Estimated median home price

$989,995
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 - 300K3
$300K - 400K27
$400K - 500K28
$500K - 600K28
$600K - 700K32
$700K - 800K21
$800K - 900K9
$900K - 1M16
$1M - Max159

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family248
Townhouse45
Condo10
Commercial1
Rental89
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/2/2026)

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 10/3/2026.