103 total properties
Did you mean the neighborhood Windermere?
View 3999 ISABELLA CIRCLE Windermere, FL MLS# O6320216
  • Virtual Tour
1 of 42
$17,950
6

Beds

6.2

Baths

6,881

Sq.Ft.

3999 ISABELLA CIRCLE

Windermere, FL

Courtesy of DELUCA REAL ESTATE SERVICES CORP
View 4303 ISABELLA CIRCLE Windermere, FL MLS# O6348386
  • Virtual Tour
1 of 77
$17,900
7

Beds

4.2

Baths

4,609

Sq.Ft.

4303 ISABELLA CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 4326 ISABELLA CIRCLE Windermere, FL MLS# O6378933
  • Virtual Tour
1 of 8
$16,000
5

Beds

5.1

Baths

5,507

Sq.Ft.

4326 ISABELLA CIRCLE

Windermere, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 801 W 2ND AVENUE Windermere, FL MLS# O6383208
  • Recently Listed
1 of 44
$15,000
5

Beds

6.1

Baths

5,639

Sq.Ft.

801 W 2ND AVENUE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 4012 ISABELLA CIRCLE Windermere, FL MLS# O6354060
  • Virtual Tour
1 of 71
$14,800
6

Beds

7.2

Baths

7,337

Sq.Ft.

4012 ISABELLA CIRCLE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 6219 TIROCO WAY Windermere, FL MLS# O6376831
  • Virtual Tour
1 of 41
$13,500
7

Beds

5.1

Baths

5,221

Sq.Ft.

6219 TIROCO WAY

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 6131 PAYNE STEWART DRIVE Windermere, FL MLS# O6374126
$12,000
3

Beds

3.0

Baths

2,646

Sq.Ft.

6131 PAYNE STEWART DRIVE

Windermere, FL

Courtesy of IRWIN REALTY GROUP LLC
View 5243 W LAKE BUTLER ROAD Windermere, FL MLS# O6362021
$10,999
3

Beds

3.0

Baths

3,255

Sq.Ft.

5243 W LAKE BUTLER ROAD

Windermere, FL

Courtesy of 407 PROPERTIES
View 606 E 6TH AVENUE Windermere, FL MLS# O6381054
  • Recently Listed with Virtual Tour
1 of 57
$10,500
4

Beds

4.1

Baths

4,471

Sq.Ft.

606 E 6TH AVENUE

Windermere, FL

Courtesy of ELITE GLOBAL REAL ESTATE LLC
View 1115 ESTANCIA WOODS LOOP Windermere, FL MLS# O6382762
  • Recently Listed with Virtual Tour
1 of 23
$9,850
4

Beds

4.1

Baths

4,239

Sq.Ft.

1115 ESTANCIA WOODS LOOP

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 6533 CARTMEL LANE Windermere, FL MLS# O6366042
  • Virtual Tour
1 of 31
$9,500
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY FL
View 5510 MARLEON DRIVE Windermere, FL MLS# O6382455
  • Recently Listed with Virtual Tour
1 of 38
$8,495
5

Beds

5.0

Baths

4,219

Sq.Ft.

5510 MARLEON DRIVE

Windermere, FL

Courtesy of RE/MAX ASSURED
View 2844 MIDSUMMER DRIVE Windermere, FL MLS# O6371115
$7,500
4

Beds

3.1

Baths

3,328

Sq.Ft.

2844 MIDSUMMER DRIVE

Windermere, FL

Courtesy of WINDERMERE COCOA BEACH CENTER
View 311 E 8TH AVENUE Windermere, FL MLS# O6364016
  • Virtual Tour
1 of 54
$6,500
5

Beds

4.0

Baths

3,805

Sq.Ft.

311 E 8TH AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 11539 BRICKYARD POND LANE Windermere, FL MLS# O6377340
$6,000
5

Beds

4.0

Baths

3,659

Sq.Ft.

11539 BRICKYARD POND LANE

Windermere, FL

Courtesy of PM ELITE REALTY LLC
View 6146 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379977
$6,000
7

Beds

5.0

Baths

4,751

Sq.Ft.

6146 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 11560 CLAYMONT CIRCLE Windermere, FL MLS# S5143964
  • Recently Listed with Virtual Tour
1 of 40
$6,000
4

Beds

4.1

Baths

3,512

Sq.Ft.

11560 CLAYMONT CIRCLE

Windermere, FL

Courtesy of WATSON REALTY CORP.
View 6557 CRESTMONT GLEN LANE Windermere, FL MLS# O6373926
$5,950
4

Beds

3.1

Baths

3,268

Sq.Ft.

6557 CRESTMONT GLEN LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 307 W 4TH AVENUE Windermere, FL MLS# O6275058
  • Virtual Tour
1 of 56
$5,900
4

Beds

3.0

Baths

3,190

Sq.Ft.

307 W 4TH AVENUE

Windermere, FL

Courtesy of MAINFRAME REAL ESTATE
View 12860 LAKE SAWYER LANE Windermere, FL MLS# O6317050
  • Adult Community with Virtual Tour
1 of 50
$5,800
3

Beds

2.0

Baths

1,725

Sq.Ft.

12860 LAKE SAWYER LANE

Windermere, FL

Courtesy of CROWN REALTY COMPANY

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

299

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 19
$400K - 500K 22
$500K - 600K 27
$600K - 700K 25
$700K - 800K 24
$800K - 900K 20
$900K - 1M 10
$1M - Max 152

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 246
Townhouse 32
Condo 7
Commercial 1
Rental 103
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 2/24/2026)

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 2/25/2026.