283 total properties
Did you mean the neighborhood Windermere?
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 7522 DEREXA DRIVE Windermere, FL MLS# O6373333
  • Recently Listed with Virtual Tour
1 of 62
OPEN HOUSE: Saturday 1/17 1:00 PM - 4:00 PM
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View 11578 ASHLIN PARK BOULEVARD Windermere, FL MLS# O6373714
  • Recently Listed with Virtual Tour
1 of 58
OPEN HOUSE: Sunday 1/18 1:00 PM - 4:00 PM
$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
View 12860 PENSHURST LANE Windermere, FL MLS# O6372985
  • Recently Listed with Virtual Tour
1 of 36
$480,000
4

Beds

2.1

Baths

2,460

Sq.Ft.

12860 PENSHURST LANE

Windermere, FL

Courtesy of EXP REALTY LLC
View 13366 ABUELA ALLEY Windermere, FL MLS# O6374298
  • Recently Listed with Virtual Tour
1 of 35
$444,000
3

Beds

2.1

Baths

1,589

Sq.Ft.

13366 ABUELA ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 8180 BOAT HOOK LOOP 108/301 Windermere, FL MLS# TB8465266
  • Recently Listed with Virtual Tour
1 of 27
$335,555
3

Beds

2.0

Baths

1,442

Sq.Ft.

8180 BOAT HOOK LOOP 108/301

Windermere, FL

Courtesy of EXP REALTY LLC
View 5074 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6373191
$7,595,000
5

Beds

6.1

Baths

6,937

Sq.Ft.

5074 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of MEMARPOURI REALTY LLC
View 13369 GORGONA ISLE DRIVE Windermere, FL MLS# O6373676
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Saturday 1/17 10:00 AM - 12:00 PM
$459,900
3

Beds

2.1

Baths

1,767

Sq.Ft.

13369 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 4825 PALM TREE COURT Windermere, FL MLS# O6373341
  • Recently Listed with Virtual Tour
1 of 41
$677,500
4

Beds

2.1

Baths

2,100

Sq.Ft.

4825 PALM TREE COURT

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 11675 SNAIL KITE WAY Windermere, FL MLS# O6373317
  • Recently Listed
1 of 46
$596,400
3

Beds

2.1

Baths

2,139

Sq.Ft.

11675 SNAIL KITE WAY

Windermere, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 14421 CREST PALM AVENUE Windermere, FL MLS# G5106601
  • New Construction
1 of 4
$1,069,000
4

Beds

3.1

Baths

3,404

Sq.Ft.

14421 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11472 PARK AVENUE AVENUE NE Windermere, FL MLS# G5105731
$1,400,000
5

Beds

3.1

Baths

3,166

Sq.Ft.

11472 PARK AVENUE AVENUE NE

Windermere, FL

Courtesy of Clermont - WEICHERT, REALTORS® - Hallmark Properties
View 84 OAKDALE ST Windermere, FL MLS# O6372842
  • Recently Listed
1 of 19
$1,995,000
4

Beds

4.2

Baths

3,519

Sq.Ft.

84 OAKDALE ST

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 13232 LONGACRE DRIVE Windermere, FL MLS# O6372809
  • Recently Listed with Virtual Tour
1 of 28
$710,000
5

Beds

3.0

Baths

2,511

Sq.Ft.

13232 LONGACRE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6331 LITTLE LAKE SAWYER DRIVE Windermere, FL MLS# O6372786
  • Recently Listed with Virtual Tour
1 of 10
$950,000
Studio

Beds

0.0

Baths

6331 LITTLE LAKE SAWYER DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 12862 LANGSTAFF DRIVE Windermere, FL MLS# O6372097
  • Recently Listed with Virtual Tour
1 of 45
OPEN HOUSE: Saturday 1/17 12:00 PM - 3:00 PM
$405,000
3

Beds

2.1

Baths

1,480

Sq.Ft.

12862 LANGSTAFF DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 4345 SALTMARSH SPARROW DRIVE Windermere, FL MLS# O6372774
  • Recently Listed with Virtual Tour
1 of 39
$830,000
6

Beds

5.1

Baths

3,698

Sq.Ft.

4345 SALTMARSH SPARROW DRIVE

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 13519 BICTON LANE Windermere, FL MLS# O6372084
  • Recently Listed with Virtual Tour
1 of 54
$749,000
4

Beds

3.1

Baths

2,594

Sq.Ft.

13519 BICTON LANE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE GROUP

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

281

Estimated median home price

$1,045,000
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 20
$400K - 500K 22
$500K - 600K 19
$600K - 700K 28
$700K - 800K 19
$800K - 900K 15
$900K - 1M 13
$1M - Max 144

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 224
Townhouse 34
Condo 8
Commercial 1
Rental 110
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 1/16/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 1/16/2026.

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 1/16/2026.

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 1/16/2026.