313 total properties
Did you mean the neighborhood Windermere?
View 8867 HERENCIA ALLEY Windermere, FL MLS# O6449612
  • Recently Listed with Virtual Tour
1 of 35
$405,000
3

Beds

2.1

Baths

1,382

Sq.Ft.

8867 HERENCIA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 7231 SANGALLA DRIVE Windermere, FL MLS# O6447329
  • Recently Listed with Virtual Tour
1 of 67
$1,348,000
5

Beds

4.1

Baths

3,835

Sq.Ft.

7231 SANGALLA DRIVE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 5944 CAYMUS LOOP Windermere, FL MLS# O6448123
  • Recently Listed with Virtual Tour
1 of 45
$1,050,000
4

Beds

3.0

Baths

2,984

Sq.Ft.

5944 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 8276 MARITIME FLAG ST 1204 Windermere, FL MLS# O6449170
  • Recently Listed with Virtual Tour
1 of 31
$324,900
3

Beds

2.0

Baths

1,455

Sq.Ft.

8276 MARITIME FLAG ST 1204

Windermere, FL

Courtesy of HOMEVEST REALTY
View 6544 CARTMEL LANE Windermere, FL MLS# O6447314
$2,390,000
5

Beds

4.1

Baths

4,185

Sq.Ft.

6544 CARTMEL LANE

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 8576 POWDER RIDGE TRAIL Windermere, FL MLS# O6447414
  • Recently Listed with Virtual Tour
1 of 28
$597,000
4

Beds

3.1

Baths

2,661

Sq.Ft.

8576 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11963 VERMILLION AVENUE Windermere, FL MLS# O6447919
  • Recently Listed with Virtual Tour
1 of 35
$430,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

11963 VERMILLION AVENUE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 12785 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6442356
  • Recently Listed with Virtual Tour
1 of 42
$769,000
4

Beds

3.1

Baths

2,996

Sq.Ft.

12785 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 8168 BOAT HOOK LOOP 302 Windermere, FL MLS# O6445290
$297,997
2

Beds

2.0

Baths

1,161

Sq.Ft.

8168 BOAT HOOK LOOP 302

Windermere, FL

Courtesy of BLUE KEY PROPERTY MANAGEMENT
View 8179 MARITIME FLAG STREET 206 Windermere, FL MLS# O6447793
$350,000
3

Beds

2.0

Baths

1,332

Sq.Ft.

8179 MARITIME FLAG STREET 206

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9602 MAYWOOD DRIVE Windermere, FL MLS# O6446848
$4,350,000
5

Beds

5.0

Baths

5,305

Sq.Ft.

9602 MAYWOOD DRIVE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE GROUP
View 6858 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6447605
$595,000
3

Beds

2.0

Baths

2,115

Sq.Ft.

6858 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 7030 MAPPERTON DRIVE Windermere, FL MLS# O6447067
$649,000
4

Beds

2.1

Baths

2,455

Sq.Ft.

7030 MAPPERTON DRIVE

Windermere, FL

Courtesy of FOLIO REALTY LLC
View 8229 TIBET BUTLER DRIVE Windermere, FL MLS# O6447628
$1,999,000
4

Beds

4.0

Baths

3,912

Sq.Ft.

8229 TIBET BUTLER DRIVE

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 104 E 1ST AVENUE Windermere, FL MLS# O6442932
  • Virtual Tour
1 of 53
$1,280,000
4

Beds

2.1

Baths

2,441

Sq.Ft.

104 E 1ST AVENUE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 8524 VIVARO ISLE WAY Windermere, FL MLS# G5118124
$950,000
4

Beds

3.0

Baths

2,680

Sq.Ft.

8524 VIVARO ISLE WAY

Windermere, FL

Courtesy of SERHANT
View 5092 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6446272
$8,500,000
4

Beds

5.0

Baths

7,100

Sq.Ft.

5092 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 1221 OAKDALE STREET Windermere, FL MLS# O6446547
$1,250,000
0.0

Baths

1221 OAKDALE STREET

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 12722 S LAKE SAWYER LANE Windermere, FL MLS# O6437802
$2,400,000
5

Beds

4.0

Baths

5,139

Sq.Ft.

12722 S LAKE SAWYER LANE

Windermere, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 6113 GROSVENOR SHORE DRIVE Windermere, FL MLS# O6443311
$6,950,000
7

Beds

6.2

Baths

8,722

Sq.Ft.

6113 GROSVENOR SHORE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY

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

312

Estimated median home price

$1,089,500
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 - 100K1
$100K - 200K0
$200K - 300K4
$300K - 400K26
$400K - 500K23
$500K - 600K29
$600K - 700K33
$700K - 800K15
$800K - 900K7
$900K - 1M12
$1M - Max162

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family239
Townhouse40
Condo11
Commercial1
Rental104
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/29/2026)

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 10/29/2026.