93 total properties
Did you mean the neighborhood Windermere?
View 8520 GREENBANK BOULEVARD Windermere, FL MLS# O6396741
$3,150
3

Beds

2.0

Baths

1,726

Sq.Ft.

8520 GREENBANK BOULEVARD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
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 1243 DINGENS AVENUE Windermere, FL MLS# O6300024
$3,000
4

Beds

3.0

Baths

1,928

Sq.Ft.

1243 DINGENS AVENUE

Windermere, FL

Courtesy of REALMULTIPROPERTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 8602 VIA TAVOLERIA WAY Windermere, FL MLS# O6404174
  • Recently Listed with Virtual Tour
1 of 16
$3,000
4

Beds

3.1

Baths

1,936

Sq.Ft.

8602 VIA TAVOLERIA WAY

Windermere, FL

Courtesy of U KEY REALTY
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 8320 BRYCE CANYON AVENUE Windermere, FL MLS# O6396080
$2,950
4

Beds

2.1

Baths

2,047

Sq.Ft.

8320 BRYCE CANYON AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 10612 REAMS ROAD Windermere, FL MLS# O6408707
  • Recently Listed with Virtual Tour
1 of 46
$2,950
3

Beds

2.1

Baths

1,829

Sq.Ft.

10612 REAMS ROAD

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 14200 OASIS COVE BOULEVARD 3301 Windermere, FL MLS# S5145300
$2,900
4

Beds

2.1

Baths

1,638

Sq.Ft.

14200 OASIS COVE BOULEVARD 3301

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 9109 LEGADO DRIVE Windermere, FL MLS# O6408400
  • Recently Listed with Virtual Tour
1 of 37
$2,900
3

Beds

2.1

Baths

1,687

Sq.Ft.

9109 LEGADO DRIVE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE GROUP
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 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 12030 SILVERLAKE PARK DRIVE Windermere, FL MLS# S5148671
$2,850
4

Beds

2.1

Baths

2,068

Sq.Ft.

12030 SILVERLAKE PARK DRIVE

Windermere, FL

Courtesy of TOPSKY REALTY INC
View 8642 POWDER RIDGE TRAIL Windermere, FL MLS# O6401509
  • Recently Listed with Virtual Tour
1 of 30
$2,850
4

Beds

2.1

Baths

1,890

Sq.Ft.

8642 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of METRO CITY REALTY
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 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 8470 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5147220
$2,800
3

Beds

2.1

Baths

1,644

Sq.Ft.

8470 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of LPT REALTY, LLC
View 7255 SHADEVIEW ALLEY Windermere, FL MLS# O6395878
$2,795
3

Beds

2.1

Baths

1,593

Sq.Ft.

7255 SHADEVIEW ALLEY

Windermere, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 12357 VIA DERNA PLACE Windermere, FL MLS# O6405969
  • Recently Listed with Virtual Tour
1 of 33
$2,750
3

Beds

2.1

Baths

1,919

Sq.Ft.

12357 VIA DERNA PLACE

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
View 9031 LEGADO DRIVE Windermere, FL MLS# O6404941
  • Recently Listed with Virtual Tour
1 of 27
$2,750
3

Beds

2.1

Baths

1,547

Sq.Ft.

9031 LEGADO DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7652 RIPPLEPOINTE WAY Windermere, FL MLS# O6409167
  • Recently Listed with Virtual Tour
1 of 22
$2,750
3

Beds

2.1

Baths

1,743

Sq.Ft.

7652 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of ADVANCE REALTY & MANAGEMENT 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

341

Estimated median home price

$1,196,000
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 - 300K2
$300K - 400K17
$400K - 500K23
$500K - 600K31
$600K - 700K19
$700K - 800K25
$800K - 900K19
$900K - 1M16
$1M - Max189

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family287
Townhouse35
Condo6
Commercial1
Rental90
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/21/2026)

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 5/21/2026.