95 total properties
Did you mean the neighborhood Windermere?
View 4542 BLUE MAJOR DRIVE Windermere, FL MLS# O6392465
$3,100
4

Beds

2.1

Baths

2,618

Sq.Ft.

4542 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 935 LASCALA DRIVE Windermere, FL MLS# O6391352
  • Virtual Tour
1 of 30
$2,495
3

Beds

2.0

Baths

1,601

Sq.Ft.

935 LASCALA DRIVE

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 4818 BREEZY PALMS COURT Windermere, FL MLS# O6391402
$2,799
3

Beds

2.0

Baths

1,492

Sq.Ft.

4818 BREEZY PALMS COURT

Windermere, FL

Courtesy of 407 PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 12807 CRAGSIDE LANE Windermere, FL MLS# S5145998
$3,000
4

Beds

2.0

Baths

2,151

Sq.Ft.

12807 CRAGSIDE LANE

Windermere, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 11051 CONISTON WAY Windermere, FL MLS# O6392514
$13,500
5

Beds

5.1

Baths

5,498

Sq.Ft.

11051 CONISTON WAY

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8476 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5145826
$2,950
3

Beds

2.1

Baths

1,700

Sq.Ft.

8476 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 8913 MATRIARCA ALY Windermere, FL MLS# S5145953
  • New Construction with Virtual Tour
1 of 30
$2,650
3

Beds

2.1

Baths

1,556

Sq.Ft.

8913 MATRIARCA ALY

Windermere, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 7307 PENKRIDGE LANE Windermere, FL MLS# O6384396
$2,800
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 11434 JASPER KAY TERRACE 206 Windermere, FL MLS# O6390889
$2,250
3

Beds

2.0

Baths

1,455

Sq.Ft.

11434 JASPER KAY TERRACE 206

Windermere, FL

Courtesy of MNT INTERNATIONAL
View 8408 ABBOTSBURY DRIVE Windermere, FL MLS# O6388448
$2,950
4

Beds

3.0

Baths

2,343

Sq.Ft.

8408 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
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
$3,400
4

Beds

2.1

Baths

3,011

Sq.Ft.

12761 BIDEFORD AVENUE

Windermere, FL

Courtesy of SHINING OAK REALTY
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
$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 13040 OVERSTREET ROAD Windermere, FL MLS# S5144750
$2,795
3

Beds

2.1

Baths

2,203

Sq.Ft.

13040 OVERSTREET ROAD

Windermere, FL

Courtesy of MULTI CHOICE 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 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

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

356

Estimated median home price

$1,104,995
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 - 300K1
$300K - 400K21
$400K - 500K24
$500K - 600K39
$600K - 700K25
$700K - 800K24
$800K - 900K22
$900K - 1M17
$1M - Max183

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family298
Townhouse38
Condo7
Commercial1
Rental95
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/30/2026)

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 4/30/2026.