95 total properties
Did you mean the neighborhood Windermere?
View 8936 MATRIARCA ALLEY Windermere, FL MLS# O6394582
$2,600
3

Beds

2.1

Baths

1,696

Sq.Ft.

8936 MATRIARCA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 12563 CRAGSIDE LANE Windermere, FL MLS# O6394594
$2,995
4

Beds

2.1

Baths

2,460

Sq.Ft.

12563 CRAGSIDE LANE

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 812 EAST BOULEVARD Windermere, FL MLS# O6394559
  • Recently Listed with Virtual Tour
1 of 100
$7,000
2

Beds

2.0

Baths

1,680

Sq.Ft.

812 EAST BOULEVARD

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 9313 PALM TREE DRIVE Windermere, FL MLS# O6394430
$2,850
3

Beds

2.0

Baths

1,489

Sq.Ft.

9313 PALM TREE DRIVE

Windermere, FL

Courtesy of FHG REALTY, LLC
View 6876 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6394242
  • Recently Listed with Virtual Tour
1 of 44
$3,100
4

Beds

2.1

Baths

2,781

Sq.Ft.

6876 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 13466 ZORI LANE Windermere, FL MLS# O6393575
  • Virtual Tour
1 of 42
$4,500
4

Beds

3.0

Baths

2,813

Sq.Ft.

13466 ZORI LANE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12863 HOLDENBURY LANE Windermere, FL MLS# O6393800
$2,850
3

Beds

2.0

Baths

2,148

Sq.Ft.

12863 HOLDENBURY LANE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 12803 HOLDENBURY LANE Windermere, FL MLS# O6389377
$3,200
4

Beds

2.1

Baths

2,439

Sq.Ft.

12803 HOLDENBURY LANE

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 13231 OVERSTREET ROAD Windermere, FL MLS# O6392297
$2,850
3

Beds

2.1

Baths

2,306

Sq.Ft.

13231 OVERSTREET ROAD

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
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 14478 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL MLS# O6393609
$2,500
4

Beds

2.1

Baths

1,628

Sq.Ft.

14478 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
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
$2,849
3

Beds

2.0

Baths

1,492

Sq.Ft.

4818 BREEZY PALMS COURT

Windermere, FL

Courtesy of 407 PROPERTIES
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 8921 NEWMARKET DRIVE Windermere, FL MLS# O6390585
$2,350
3

Beds

2.1

Baths

1,429

Sq.Ft.

8921 NEWMARKET DRIVE

Windermere, FL

Courtesy of GOLDEN PACIFIC REALTY INC
View 8913 MATRIARCA ALY Windermere, FL MLS# S5145953
  • New Construction with Virtual Tour
1 of 30
$2,800
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.

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

353

Estimated median home price

$1,019,990
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 - 400K18
$400K - 500K26
$500K - 600K35
$600K - 700K30
$700K - 800K25
$800K - 900K20
$900K - 1M21
$1M - Max177

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family295
Townhouse36
Condo8
Commercial1
Rental96
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/18/2026)

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 4/19/2026.