92 total properties
Did you mean the neighborhood Windermere?
View 7307 PENKRIDGE LANE Windermere, FL MLS# O6384396
  • Recently Listed with Virtual Tour
1 of 38
$2,900
4

Beds

2.1

Baths

1,997

Sq.Ft.

7307 PENKRIDGE LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7135 THICKET BRANCH ALLEY Windermere, FL MLS# O6389351
$2,600
3

Beds

2.1

Baths

1,569

Sq.Ft.

7135 THICKET BRANCH ALLEY

Windermere, FL

Courtesy of JULIAN PROPERTIES, INC.
View 13643 LAKE CAWOOD DRIVE Windermere, FL MLS# O6389529
  • Recently Listed with Virtual Tour
1 of 78
$12,800
8

Beds

7.1

Baths

8,203

Sq.Ft.

13643 LAKE CAWOOD DRIVE

Windermere, FL

Courtesy of JWJ REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 11434 JASPER KAY TERRACE 206 Windermere, FL MLS# O6390889
  • Recently Listed with Virtual Tour
1 of 45
$2,350
3

Beds

2.0

Baths

1,455

Sq.Ft.

11434 JASPER KAY TERRACE 206

Windermere, FL

Courtesy of MNT INTERNATIONAL
View 11456 CENTER LAKE DRIVE Windermere, FL MLS# O6388958
$2,550
3

Beds

2.1

Baths

1,881

Sq.Ft.

11456 CENTER LAKE DRIVE

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 14200 OASIS COVE BOULEVARD 3301 Windermere, FL MLS# S5145300
$3,000
4

Beds

2.1

Baths

1,638

Sq.Ft.

14200 OASIS COVE BOULEVARD 3301

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 12761 BIDEFORD AVENUE Windermere, FL MLS# O6387477
$3,500
4

Beds

2.1

Baths

3,011

Sq.Ft.

12761 BIDEFORD AVENUE

Windermere, FL

Courtesy of SHINING OAK REALTY
View 1602 ROBERTS LANDING ROAD Windermere, FL MLS# O6387865
$3,000
4

Beds

2.0

Baths

2,352

Sq.Ft.

1602 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of ASA FLORIDA PROPERTIES INC
View 8532 BOWDEN WAY Windermere, FL MLS# O6380872
$9,800
4

Beds

4.0

Baths

3,885

Sq.Ft.

8532 BOWDEN WAY

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8973 MATRIARCA ALLEY Windermere, FL MLS# O6387553
  • Recently Listed with Virtual Tour
1 of 29
$2,650
3

Beds

2.1

Baths

1,690

Sq.Ft.

8973 MATRIARCA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 7314 BRIGHTLAND STREET Windermere, FL MLS# O6386905
$2,450
3

Beds

2.1

Baths

1,720

Sq.Ft.

7314 BRIGHTLAND STREET

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 14235 DESERT HAVEN STREET 3503 Windermere, FL MLS# O6386593
$2,750
3

Beds

2.1

Baths

2,028

Sq.Ft.

14235 DESERT HAVEN STREET 3503

Windermere, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 13040 OVERSTREET ROAD Windermere, FL MLS# S5144750
$2,900
3

Beds

2.1

Baths

2,203

Sq.Ft.

13040 OVERSTREET ROAD

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
View 721 MAGNOLIA STREET Windermere, FL MLS# S5144805
$2,250
2

Beds

1.0

Baths

891

Sq.Ft.

721 MAGNOLIA STREET

Windermere, FL

Courtesy of EXP REALTY LLC
View 13845 ANCILLA BOULEVARD Windermere, FL MLS# O6386180
$2,435
2

Beds

2.0

Baths

1,155

Sq.Ft.

13845 ANCILLA BOULEVARD

Windermere, FL

Courtesy of CT HOMES REALTY CORPORATION
View 13841 ANCILLA BOULEVARD Windermere, FL MLS# O6386275
$2,695
3

Beds

2.1

Baths

2,332

Sq.Ft.

13841 ANCILLA BOULEVARD

Windermere, FL

Courtesy of CT HOMES REALTY CORPORATION
View 12925 HOLDENBURY LANE Windermere, FL MLS# O6385584
$3,500
4

Beds

2.1

Baths

2,981

Sq.Ft.

12925 HOLDENBURY LANE

Windermere, FL

Courtesy of INTEREALTY SERVICE
View 9701 LAKE ISLEWORTH COURT Windermere, FL MLS# O6385693
$12,500
3

Beds

3.0

Baths

3,535

Sq.Ft.

9701 LAKE ISLEWORTH COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 9005 VIA DI CANTI UNIT A DRIVE Windermere, FL MLS# O6383666
$2,700
4

Beds

3.0

Baths

1,955

Sq.Ft.

9005 VIA DI CANTI UNIT A DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 12813 GRACEHILL LANE Windermere, FL MLS# O6385408
$2,750
3

Beds

2.1

Baths

1,748

Sq.Ft.

12813 GRACEHILL LANE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC

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

336

Estimated median home price

$1,024,995
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 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K17
$400K - 500K24
$500K - 600K35
$600K - 700K29
$700K - 800K23
$800K - 900K23
$900K - 1M16
$1M - Max169

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family281
Townhouse34
Condo6
Commercial1
Rental91
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/27/2026)

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 3/29/2026.