308 total properties
Did you mean the neighborhood Windermere?
View 8630 POWDER RIDGE TRAIL Windermere, FL MLS# C7529514
$528,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8630 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of SUNCOAST CHOICE REALTY
View 13738 EDEN ISLE BOULEVARD Windermere, FL MLS# S5158063
$530,000
4

Beds

2.0

Baths

2,020

Sq.Ft.

13738 EDEN ISLE BOULEVARD

Windermere, FL

Courtesy of THE PROPERTY FIRM
View 4936 WISE BIRD DRIVE Windermere, FL MLS# O6450351
  • Recently Listed with Virtual Tour
1 of 73
$535,000
4

Beds

3.0

Baths

2,361

Sq.Ft.

4936 WISE BIRD DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 9433 PALM TREE DRIVE Windermere, FL MLS# O6423262
$539,900
3

Beds

2.0

Baths

1,819

Sq.Ft.

9433 PALM TREE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 1661 ROBERTS LANDING ROAD Windermere, FL MLS# O6407725
$549,900
0.0

Baths

1661 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13317 LUSH LIME ALLEY Windermere, FL MLS# TB8551016
  • New Construction with Virtual Tour
1 of 20
OPEN HOUSE: Saturday 10/24 12:00 PM - 4:00 PM
$549,990
3

Beds

2.1

Baths

1,699

Sq.Ft.

13317 LUSH LIME ALLEY

Windermere, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 13137 PENSHURST LANE Windermere, FL MLS# O6421270
  • Virtual Tour
1 of 48
OPEN HOUSE: Saturday 10/24 5:00 PM - 7:00 PM
$550,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13137 PENSHURST LANE

Windermere, FL

Courtesy of MORRIS WILLIAMS REALTY
View 9021 VIA DI CANTI Windermere, FL MLS# O6437659
  • Virtual Tour
1 of 33
$550,000
5

Beds

3.1

Baths

2,268

Sq.Ft.

9021 VIA DI CANTI

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 9319 WOODBREEZE BOULEVARD Windermere, FL MLS# O6384930
$554,555
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13219 CHARFIELD STREET Windermere, FL MLS# O6420991
$555,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13219 CHARFIELD STREET

Windermere, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 13321 LUSH LIME ALLEY Windermere, FL MLS# TB8542700
  • New Construction with Virtual Tour
1 of 21
$556,256
3

Beds

2.1

Baths

1,649

Sq.Ft.

13321 LUSH LIME ALLEY

Windermere, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 4827 FLINT ROAD Windermere, FL MLS# O6449449
  • Recently Listed with Virtual Tour
1 of 39
$559,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4827 FLINT ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 8225 BRYCE CANYON AVENUE Windermere, FL MLS# O6371960
$560,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

8225 BRYCE CANYON AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 11543 CHARNOCK DRIVE Windermere, FL MLS# S5158277
$560,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

11543 CHARNOCK DRIVE

Windermere, FL

Courtesy of PM ELITE REALTY LLC
View 7271 LONDALE BOULEVARD Windermere, FL MLS# O6445539
  • Virtual Tour
1 of 47
OPEN HOUSE: Wednesday 10/21 9:00 AM - 7:00 PM
$562,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

7271 LONDALE BOULEVARD

Windermere, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 9802 6TH AVENUE Windermere, FL MLS# O6349678
$575,000
0.0

Baths

9802 6TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 6828 HELMSLEY CIRCLE Windermere, FL MLS# O6435655
$575,000
4

Beds

3.0

Baths

2,064

Sq.Ft.

6828 HELMSLEY CIRCLE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 13231 ROXBORO ROAD Windermere, FL MLS# O6427997
$579,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13231 ROXBORO ROAD

Windermere, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 9011 CHAPMAN OAK COURT Windermere, FL MLS# S5148031
  • Adult Community with Virtual Tour
1 of 30
$584,900
4

Beds

2.0

Baths

2,050

Sq.Ft.

9011 CHAPMAN OAK COURT

Windermere, FL

Courtesy of TOWNE CENTER REALTY
View 1516 HEMPEL AVENUE Windermere, FL MLS# O6342593
$595,000
0.0

Baths

1516 HEMPEL AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

308

Estimated median home price

$1,052,500
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 - 100K1
$100K - 200K0
$200K - 300K4
$300K - 400K28
$400K - 500K23
$500K - 600K28
$600K - 700K33
$700K - 800K17
$800K - 900K7
$900K - 1M11
$1M - Max156

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family231
Townhouse41
Condo13
Commercial1
Rental101
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/21/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/22/2026.