91 total properties
Did you mean the neighborhood Windermere?
View 14478 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL MLS# O6393609
  • Recently Listed with Virtual Tour
1 of 33
$2,500
4

Beds

2.1

Baths

1,628

Sq.Ft.

14478 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 13285 GORGONA ISLE DRIVE Windermere, FL MLS# O6379997
$2,600
3

Beds

2.1

Baths

1,547

Sq.Ft.

13285 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of REALTY HUB
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.
The time to sell is now! THE TIME TO SELL IS NOW!
View 11642 WATER RUN ALLEY Windermere, FL MLS# S5141662
$2,650
3

Beds

2.1

Baths

1,624

Sq.Ft.

11642 WATER RUN ALLEY

Windermere, FL

Courtesy of VS INTERNATIONAL PROPERTIES
View 12623 LANGSTAFF DRIVE Windermere, FL MLS# O6383047
$2,650
2

Beds

2.1

Baths

1,239

Sq.Ft.

12623 LANGSTAFF DRIVE

Windermere, FL

Courtesy of ELITE REALTY ENTERPRISES LLC
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 8936 MATRIARCA ALLEY Windermere, FL MLS# O6394582
  • Recently Listed with Virtual Tour
1 of 19
$2,650
3

Beds

2.1

Baths

1,696

Sq.Ft.

8936 MATRIARCA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
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 11619 WATER RUN ALLEY Windermere, FL MLS# O6384489
  • New Construction with Virtual Tour
1 of 31
$2,700
3

Beds

2.1

Baths

1,570

Sq.Ft.

11619 WATER RUN ALLEY

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
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 13718 BECKMAN DRIVE Windermere, FL MLS# S5136490
$2,750
3

Beds

2.1

Baths

1,912

Sq.Ft.

13718 BECKMAN DRIVE

Windermere, FL

Courtesy of MD3 HOMES LLC
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
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 7681 FORDSON LANE Windermere, FL MLS# O6344027
  • Virtual Tour
1 of 18
$2,800
4

Beds

2.1

Baths

1,997

Sq.Ft.

7681 FORDSON LANE

Windermere, FL

Courtesy of REILE REALTY CORP
View 7609 SUTHERTON LANE Windermere, FL MLS# O6382713
$2,800
3

Beds

2.1

Baths

1,545

Sq.Ft.

7609 SUTHERTON LANE

Windermere, FL

Courtesy of 1 ELEVEN REALTY
View 8913 MATRIARCA ALY Windermere, FL MLS# S5145953
  • Recently Listed 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 7612 FAIRGROVE AVENUE Windermere, FL MLS# S5143482
$2,850
3

Beds

2.1

Baths

1,742

Sq.Ft.

7612 FAIRGROVE AVENUE

Windermere, FL

Courtesy of FLORIDA FANTASY REAL ESTATE INC
View 12225 JOSHUA TREE TRAIL Windermere, FL MLS# O6392136
$2,850
3

Beds

2.1

Baths

1,833

Sq.Ft.

12225 JOSHUA TREE TRAIL

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 13231 OVERSTREET ROAD Windermere, FL MLS# O6392297
  • Recently Listed with Virtual Tour
1 of 16
$2,850
3

Beds

2.1

Baths

2,306

Sq.Ft.

13231 OVERSTREET ROAD

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 12863 HOLDENBURY LANE Windermere, FL MLS# O6393800
  • Recently Listed with Virtual Tour
1 of 6
$2,850
3

Beds

2.0

Baths

2,148

Sq.Ft.

12863 HOLDENBURY LANE

Windermere, FL

Courtesy of LPT REALTY, LLC

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

342

Estimated median home price

$1,000,000
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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K19
$400K - 500K24
$500K - 600K35
$600K - 700K30
$700K - 800K24
$800K - 900K23
$900K - 1M17
$1M - Max170

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family286
Townhouse38
Condo4
Commercial1
Rental90
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/31/2026)

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 4/1/2026.