38 total properties
Did you mean the neighborhood Windermere?
View 6206 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6451210
$580,000
3

Beds

2.1

Baths

1,984

Sq.Ft.

6206 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of ATRIUM REALTY, LLC
View 13731 CALERA ALLEY Windermere, FL MLS# O6452681
  • Recently Listed with Virtual Tour
1 of 53
$465,000
3

Beds

2.1

Baths

2,113

Sq.Ft.

13731 CALERA ALLEY

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5231 LEMON TWIST LANE Windermere, FL MLS# S5160165
  • Recently Listed with Virtual Tour
1 of 20
$559,900
4

Beds

3.1

Baths

2,311

Sq.Ft.

5231 LEMON TWIST LANE

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 4936 WISE BIRD DRIVE Windermere, FL MLS# O6450351
$535,000
4

Beds

3.0

Baths

2,361

Sq.Ft.

4936 WISE BIRD DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13125 PENSHURST LANE Windermere, FL MLS# O6449706
  • Recently Listed with Virtual Tour
1 of 42
$599,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13125 PENSHURST LANE

Windermere, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC
View 4827 FLINT ROAD Windermere, FL MLS# O6449449
  • 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 8576 POWDER RIDGE TRAIL Windermere, FL MLS# O6447414
  • Recently Listed with Virtual Tour
1 of 28
$597,000
4

Beds

3.1

Baths

2,661

Sq.Ft.

8576 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 6858 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6447605
$595,000
3

Beds

2.0

Baths

2,115

Sq.Ft.

6858 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 7271 LONDALE BOULEVARD Windermere, FL MLS# O6445539
  • Virtual Tour
1 of 47
OPEN HOUSE: Wednesday 10/28 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 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 13317 LUSH LIME ALLEY Windermere, FL MLS# TB8551016
  • New Construction with Virtual Tour
1 of 20
$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 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 13535 BRAMHAM LANE Windermere, FL MLS# S5157827
$489,900
3

Beds

2.0

Baths

1,820

Sq.Ft.

13535 BRAMHAM LANE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 12679 CALDERDALE AVENUE Windermere, FL MLS# O6442555
$520,000
3

Beds

2.0

Baths

1,681

Sq.Ft.

12679 CALDERDALE AVENUE

Windermere, FL

Courtesy of NEWKEY REAL ESTATE LLC
View 13424 HOPKINTON COURT Windermere, FL MLS# O6438808
$485,000
4

Beds

2.0

Baths

2,190

Sq.Ft.

13424 HOPKINTON COURT

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6441184
$445,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of KARDOSH REALTY
View 4844 FLINT ROAD Windermere, FL MLS# O6436938
  • Virtual Tour
1 of 20
$519,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4844 FLINT ROAD

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 11734 WATER RUN ALLEY Windermere, FL MLS# S5156211
$445,000
3

Beds

2.1

Baths

1,727

Sq.Ft.

11734 WATER RUN ALLEY

Windermere, FL

Courtesy of REMAX PREMIER PROPERTIES
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 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

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

312

Estimated median home price

$1,089,500
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 - 400K27
$400K - 500K23
$500K - 600K28
$600K - 700K33
$700K - 800K14
$800K - 900K7
$900K - 1M12
$1M - Max163

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family238
Townhouse41
Condo11
Commercial1
Rental102
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/28/2026)

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 10/28/2026.