108 total properties
Did you mean the neighborhood Windermere?
View 14235 DESERT HAVEN STREET 3503 Windermere, FL MLS# O6386593
  • Recently Listed with Virtual Tour
1 of 39
$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 8563 GREENBANK BOULEVARD Windermere, FL MLS# O6386388
  • Recently Listed
1 of 60
$3,700
4

Beds

3.1

Baths

2,666

Sq.Ft.

8563 GREENBANK BOULEVARD

Windermere, FL

Courtesy of ALVES AND HOWELL REALTY
View 13040 OVERSTREET ROAD Windermere, FL MLS# S5144750
  • Recently Listed with Virtual Tour
1 of 45
$2,900
3

Beds

2.1

Baths

2,203

Sq.Ft.

13040 OVERSTREET ROAD

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 721 MAGNOLIA STREET Windermere, FL MLS# S5144805
  • Recently Listed with Virtual Tour
1 of 13
$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
  • Recently Listed with Virtual Tour
1 of 33
$2,775
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
  • Recently Listed with Virtual Tour
1 of 28
$2,775
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
  • Recently Listed with Virtual Tour
1 of 24
$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
  • Recently Listed
1 of 31
$12,500
3

Beds

3.0

Baths

3,535

Sq.Ft.

9701 LAKE ISLEWORTH COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 8526 GREENBANK BOULEVARD Windermere, FL MLS# S5143498
  • Recently Listed with Virtual Tour
1 of 16
$2,795
3

Beds

2.0

Baths

2,190

Sq.Ft.

8526 GREENBANK BOULEVARD

Windermere, FL

Courtesy of AVID REALTY LLC
View 5510 MARLEON DRIVE Windermere, FL MLS# O6382455
  • Recently Listed with Virtual Tour
1 of 38
$8,495
5

Beds

5.0

Baths

4,219

Sq.Ft.

5510 MARLEON DRIVE

Windermere, FL

Courtesy of RE/MAX ASSURED
View 9005 VIA DI CANTI UNIT A DRIVE Windermere, FL MLS# O6383666
  • Recently Listed with Virtual Tour
1 of 24
$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 11630 VIA LUCERNA CIRCLE Windermere, FL MLS# O6385251
  • Recently Listed with Virtual Tour
1 of 7
$3,300
4

Beds

3.1

Baths

2,823

Sq.Ft.

11630 VIA LUCERNA CIRCLE

Windermere, FL

Courtesy of SANTOSHI REALTY LLC
View 12813 GRACEHILL LANE Windermere, FL MLS# O6385408
  • Recently Listed with Virtual Tour
1 of 18
$2,800
3

Beds

2.1

Baths

1,748

Sq.Ft.

12813 GRACEHILL LANE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 11619 WATER RUN ALLEY Windermere, FL MLS# O6384489
  • Recently Listed with Virtual Tour
1 of 31
$2,780
3

Beds

2.1

Baths

1,570

Sq.Ft.

11619 WATER RUN ALLEY

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 5317 KEENES PHEASANT DRIVE Windermere, FL MLS# O6384596
  • Recently Listed with Virtual Tour
1 of 31
$2,500
2

Beds

2.0

Baths

1,155

Sq.Ft.

5317 KEENES PHEASANT DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 5019 BLUE MAJOR DRIVE Windermere, FL MLS# O6382091
  • Recently Listed with Virtual Tour
1 of 20
$3,300
4

Beds

3.0

Baths

2,345

Sq.Ft.

5019 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 11562 AMIDSHIP LANE 114 Windermere, FL MLS# O6383904
  • Recently Listed with Virtual Tour
1 of 35
$2,500
3

Beds

2.0

Baths

1,455

Sq.Ft.

11562 AMIDSHIP LANE 114

Windermere, FL

Courtesy of TWIN HOMES REALTY
View 801 W 2ND AVENUE Windermere, FL MLS# O6383208
  • Recently Listed
1 of 44
$15,000
5

Beds

6.1

Baths

5,639

Sq.Ft.

801 W 2ND AVENUE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7403 FAIRGROVE AVENUE Windermere, FL MLS# O6383636
  • Recently Listed with Virtual Tour
1 of 31
$4,500
6

Beds

3.1

Baths

3,841

Sq.Ft.

7403 FAIRGROVE AVENUE

Windermere, FL

Courtesy of PABLA PROPERTIES
View 10710 REAMS ROAD Windermere, FL MLS# O6383203
  • Recently Listed with Virtual Tour
1 of 34
$2,950
4

Beds

2.1

Baths

2,092

Sq.Ft.

10710 REAMS ROAD

Windermere, FL

Courtesy of ALFANO PROPERTY MANAGEMENT

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

301

Estimated median home price

$1,050,000
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

Price Count
$0 - 100K 1
$100K - 200K 0
$200K - 300K 0
$300K - 400K 16
$400K - 500K 22
$500K - 600K 28
$600K - 700K 25
$700K - 800K 26
$800K - 900K 20
$900K - 1M 9
$1M - Max 154

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 250
Townhouse 31
Condo 5
Commercial 1
Rental 108
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 3/1/2026)

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 3/1/2026.