292 total properties
Did you mean the neighborhood Windermere?
View 5463 GEMGOLD COURT Windermere, FL MLS# O6375567
  • Recently Listed with Virtual Tour
1 of 42
$599,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

5463 GEMGOLD COURT

Windermere, FL

Courtesy of INFINITY REALTY GROUP LLC
View 14383 CREST PALM AVENUE Windermere, FL MLS# G5107222
  • Recently Listed
1 of 2
$1,176,990
6

Beds

4.0

Baths

3,550

Sq.Ft.

14383 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14285 CREST PALM AVENUE Windermere, FL MLS# G5107224
  • Recently Listed
1 of 61
$1,029,990
4

Beds

4.0

Baths

3,100

Sq.Ft.

14285 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6752 TRELLIS VINE LOOP Windermere, FL MLS# O6376318
  • Recently Listed with Virtual Tour
1 of 30
$1,050,000
5

Beds

3.1

Baths

3,820

Sq.Ft.

6752 TRELLIS VINE LOOP

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 11658 HAMPSTEAD STREET Windermere, FL MLS# O6376140
  • Recently Listed with Virtual Tour
1 of 74
$1,435,000
7

Beds

4.1

Baths

4,563

Sq.Ft.

11658 HAMPSTEAD STREET

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 12214 LANGSTAFF DRIVE Windermere, FL MLS# O6376431
  • Recently Listed with Virtual Tour
1 of 15
$389,000
3

Beds

2.1

Baths

1,545

Sq.Ft.

12214 LANGSTAFF DRIVE

Windermere, FL

Courtesy of PREMIUM REALTY GROUP USA
View 8650 ABBOTSBURY DRIVE Windermere, FL MLS# O6376488
  • Recently Listed with Virtual Tour
1 of 49
$595,000
4

Beds

3.1

Baths

2,628

Sq.Ft.

8650 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of THE AGENCY FL
View 11255 MACAW COURT Windermere, FL MLS# O6371007
  • Recently Listed with Virtual Tour
1 of 49
$2,987,500
5

Beds

5.1

Baths

5,845

Sq.Ft.

11255 MACAW COURT

Windermere, FL

Courtesy of REAL BROKER, LLC
View 6638 BRIDGEWATER VILLAGE ROAD Windermere, FL MLS# O6374429
  • Recently Listed with Virtual Tour
1 of 40
OPEN HOUSE: Saturday 1/24 12:00 PM - 3:00 PM
$674,900
4

Beds

2.1

Baths

2,908

Sq.Ft.

6638 BRIDGEWATER VILLAGE ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7451 FAIRGROVE AVENUE Windermere, FL MLS# O6375170
  • Recently Listed with Virtual Tour
1 of 46
$580,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

7451 FAIRGROVE AVENUE

Windermere, FL

Courtesy of TALENT REALTY SOLUTIONS
View 8648 POWDER RIDGE TRAIL Windermere, FL MLS# O6373065
  • Recently Listed
1 of 4
$528,000
3

Beds

2.1

Baths

1,876

Sq.Ft.

8648 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 801 W 2ND AVENUE Windermere, FL MLS# O6375693
  • Recently Listed
1 of 44
OPEN HOUSE: Saturday 1/24 1:00 PM - 3:00 PM
$4,150,000
5

Beds

6.1

Baths

5,639

Sq.Ft.

801 W 2ND AVENUE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7885 BERKSHIRE OAK ALLEY Windermere, FL MLS# O6374875
  • Recently Listed
1 of 30
$579,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7885 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of U S GLORY REALTY
View 6841 HELMSLEY CIRCLE Windermere, FL MLS# O6372635
  • Recently Listed with Virtual Tour
1 of 36
$650,000
4

Beds

3.0

Baths

2,371

Sq.Ft.

6841 HELMSLEY CIRCLE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 11994 MCKINNON ROAD Windermere, FL MLS# O6374410
  • Recently Listed with 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 13596 GORGONA ISLE DRIVE Windermere, FL MLS# O6374555
  • Recently Listed with Virtual Tour
1 of 26
$1,452,000
6

Beds

4.1

Baths

3,794

Sq.Ft.

13596 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7522 DEREXA DRIVE Windermere, FL MLS# O6373333
  • Recently Listed with Virtual Tour
1 of 62
$700,000
4

Beds

3.1

Baths

2,626

Sq.Ft.

7522 DEREXA DRIVE

Windermere, FL

Courtesy of UPWELL REALTY LLC
View 6109 ORTA COURT Windermere, FL MLS# O6374125
  • Recently Listed
1 of 64
$4,495,000
5

Beds

5.2

Baths

5,895

Sq.Ft.

6109 ORTA COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 11578 ASHLIN PARK BOULEVARD Windermere, FL MLS# O6373714
  • Recently Listed with Virtual Tour
1 of 58
$634,900
5

Beds

3.1

Baths

2,396

Sq.Ft.

11578 ASHLIN PARK BOULEVARD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 9426 PALM TREE DRIVE Windermere, FL MLS# O6373158
  • Recently Listed with Virtual Tour
1 of 29
$650,000
4

Beds

2.0

Baths

2,063

Sq.Ft.

9426 PALM TREE DRIVE

Windermere, FL

Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA

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

287

Estimated median home price

$1,000,000
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 1
$300K - 400K 19
$400K - 500K 23
$500K - 600K 23
$600K - 700K 30
$700K - 800K 19
$800K - 900K 16
$900K - 1M 13
$1M - Max 143

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 230
Townhouse 34
Condo 8
Commercial 1
Rental 97
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 1/22/2026)

Information deemed reliable but not guaranteed.

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The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 1/24/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 1/24/2026.

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 1/24/2026.