93 total properties
Did you mean the neighborhood Windermere?
View 6746 DUNCASTER STREET Windermere, FL MLS# O6381098
$3,250
4

Beds

2.1

Baths

2,830

Sq.Ft.

6746 DUNCASTER STREET

Windermere, FL

Courtesy of TOP LINE REALTY
View 13243 OVERSTREET ROAD Windermere, FL MLS# S5143317
$3,200
3

Beds

2.0

Baths

2,058

Sq.Ft.

13243 OVERSTREET ROAD

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 12803 HOLDENBURY LANE Windermere, FL MLS# O6389377
  • Recently Listed with Virtual Tour
1 of 16
$3,200
4

Beds

2.1

Baths

2,439

Sq.Ft.

12803 HOLDENBURY LANE

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 5019 BLUE MAJOR DRIVE Windermere, FL MLS# O6382091
$3,100
4

Beds

3.0

Baths

2,345

Sq.Ft.

5019 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 8476 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5145826
  • Recently Listed with Virtual Tour
1 of 23
$3,100
3

Beds

2.1

Baths

1,700

Sq.Ft.

8476 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 4542 BLUE MAJOR DRIVE Windermere, FL MLS# O6392465
  • Recently Listed with Virtual Tour
1 of 20
$3,100
4

Beds

2.1

Baths

2,618

Sq.Ft.

4542 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 11507 CHARNOCK DRIVE Windermere, FL MLS# O6380483
$3,049
4

Beds

2.1

Baths

2,214

Sq.Ft.

11507 CHARNOCK DRIVE

Windermere, FL

Courtesy of ORLANDO REALTY & PROPERTY MGNT
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 14200 OASIS COVE BOULEVARD 3301 Windermere, FL MLS# S5145300
  • Recently Listed with Virtual Tour
1 of 48
$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 4818 BREEZY PALMS COURT Windermere, FL MLS# O6391402
  • Recently Listed with Virtual Tour
1 of 27
$2,949
3

Beds

2.0

Baths

1,492

Sq.Ft.

4818 BREEZY PALMS COURT

Windermere, FL

Courtesy of 407 PROPERTIES
View 8636 POWDER RIDGE TRAIL Windermere, FL MLS# O6381991
$2,900
4

Beds

2.1

Baths

2,086

Sq.Ft.

8636 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of SHINING OAK 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 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 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
  • Recently Listed with Virtual Tour
1 of 19
$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 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 8408 ABBOTSBURY DRIVE Windermere, FL MLS# O6388448
  • Recently Listed with Virtual Tour
1 of 9
$2,800
4

Beds

3.0

Baths

2,343

Sq.Ft.

8408 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
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

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

330

Estimated median home price

$1,009,995
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 - 400K15
$400K - 500K25
$500K - 600K33
$600K - 700K30
$700K - 800K24
$800K - 900K23
$900K - 1M15
$1M - Max165

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family276
Townhouse34
Condo5
Commercial1
Rental91
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/24/2026)

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 3/25/2026.