61 total properties
Did you mean the neighborhood Windermere?
View 9237 MCDAVID COURT Windermere, FL MLS# O6382243
  • Virtual Tour
1 of 25
$798,000
4

Beds

2.1

Baths

2,269

Sq.Ft.

9237 MCDAVID COURT

Windermere, FL

Courtesy of VINTAGE REALTY GROUP LLC
View 13609 ANCILLA BOULEVARD Windermere, FL MLS# O6381542
$789,000
4

Beds

3.1

Baths

3,360

Sq.Ft.

13609 ANCILLA BOULEVARD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7123 CALM COVE COURT Windermere, FL MLS# O6380782
  • Virtual Tour
1 of 35
$814,000
4

Beds

3.1

Baths

3,044

Sq.Ft.

7123 CALM COVE COURT

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
  • Virtual Tour
1 of 76
$749,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 5018 RIVER GEM AVENUE Windermere, FL MLS# TB8469061
$785,000
3

Beds

2.1

Baths

2,379

Sq.Ft.

5018 RIVER GEM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA
View 13912 DARCHANCE ROAD Windermere, FL MLS# O6377606
  • Virtual Tour
1 of 49
$709,999
4

Beds

3.1

Baths

2,699

Sq.Ft.

13912 DARCHANCE ROAD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 9047 REFLECTION POINTE DRIVE Windermere, FL MLS# O6378672
$755,000
4

Beds

4.0

Baths

3,019

Sq.Ft.

9047 REFLECTION POINTE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
  • Virtual Tour
1 of 29
$649,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6376756
$725,000
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of U S GLORY REALTY
View 6876 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6373037
$664,000
4

Beds

2.1

Baths

2,781

Sq.Ft.

6876 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 6638 BRIDGEWATER VILLAGE ROAD Windermere, FL MLS# O6374429
$664,900
4

Beds

2.1

Baths

2,908

Sq.Ft.

6638 BRIDGEWATER VILLAGE ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 11994 MCKINNON ROAD Windermere, FL MLS# O6374410
  • Virtual Tour
1 of 57
$824,990
3

Beds

2.2

Baths

2,450

Sq.Ft.

11994 MCKINNON ROAD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 9426 PALM TREE DRIVE Windermere, FL MLS# O6373158
  • Virtual Tour
1 of 29
$660,000
4

Beds

2.0

Baths

2,063

Sq.Ft.

9426 PALM TREE DRIVE

Windermere, FL

Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA
View 11531 VICOLO LOOP Windermere, FL MLS# O6374016
  • Virtual Tour
1 of 33
$625,000
4

Beds

2.0

Baths

2,280

Sq.Ft.

11531 VICOLO LOOP

Windermere, FL

Courtesy of THE ROSENBLOOM TEAM
View 13232 LONGACRE DRIVE Windermere, FL MLS# O6372809
  • Virtual Tour
1 of 34
$689,000
5

Beds

3.0

Baths

2,511

Sq.Ft.

13232 LONGACRE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13519 BICTON LANE Windermere, FL MLS# O6372084
  • Virtual Tour
1 of 54
$727,500
4

Beds

3.1

Baths

2,594

Sq.Ft.

13519 BICTON LANE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE GROUP
View 13339 ROSKIN LANE Windermere, FL MLS# S5141148
  • Virtual Tour
1 of 54
$680,000
4

Beds

2.1

Baths

2,947

Sq.Ft.

13339 ROSKIN LANE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13649 ZORI LANE Windermere, FL MLS# O6369580
  • Virtual Tour
1 of 64
$725,000
4

Beds

4.0

Baths

3,129

Sq.Ft.

13649 ZORI LANE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 13106 ORANGE ISLE DRIVE Windermere, FL MLS# O6361057
$830,000
5

Beds

4.1

Baths

3,312

Sq.Ft.

13106 ORANGE ISLE DRIVE

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 6799 HELMSLEY CIRCLE Windermere, FL MLS# O6361417
  • Virtual Tour
1 of 61
$670,000
4

Beds

3.1

Baths

2,615

Sq.Ft.

6799 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

315

Estimated median home price

$1,037,000
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

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 15
$400K - 500K 24
$500K - 600K 32
$600K - 700K 24
$700K - 800K 25
$800K - 900K 20
$900K - 1M 15
$1M - Max 160

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 263
Townhouse 35
Condo 3
Commercial 1
Rental 94
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 3/18/2026)

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 3/24/2026.