30 total properties
Did you mean the neighborhood Windermere?
View 8237 SERENITY SPRING DRIVE 2605 Windermere, FL MLS# O6280344
$432,000
4

Beds

2.1

Baths

2,028

Sq.Ft.

8237 SERENITY SPRING DRIVE 2605

Windermere, FL

Courtesy of INT'L PROFESSIONAL REALTY INC
View 12930 VENNETTA WAY Windermere, FL MLS# O6301208
  • Virtual Tour
1 of 38
$429,900
3

Beds

2.1

Baths

1,644

Sq.Ft.

12930 VENNETTA WAY

Windermere, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 11637 Water Run ALLEY Windermere, FL MLS# O6194326
$429,000
3

Beds

2.1

Baths

1,466

Sq.Ft.

11637 Water Run ALLEY

Windermere, FL

Courtesy of LOKATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
  • Virtual Tour
1 of 18
$428,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 13808 ANCILLA BOULEVARD Windermere, FL MLS# S5139822
  • Adult Community
1 of 40
$414,999
3

Beds

2.1

Baths

1,461

Sq.Ft.

13808 ANCILLA BOULEVARD

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 12744 LANGSTAFF DRIVE Windermere, FL MLS# O6322751
  • Virtual Tour
1 of 20
$410,000
3

Beds

2.1

Baths

1,369

Sq.Ft.

12744 LANGSTAFF DRIVE

Windermere, FL

Courtesy of PROPERTY WAREHOUSES OF AMERICA
View 11818 WATER RUN ALLEY Windermere, FL MLS# O6353649
  • Virtual Tour
1 of 32
$410,000
3

Beds

2.1

Baths

1,588

Sq.Ft.

11818 WATER RUN ALLEY

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 11686 WATER RUN ALLEY Windermere, FL MLS# O6321724
  • Virtual Tour
1 of 24
$409,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11686 WATER RUN ALLEY

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 8625 COVENTRY PARK WAY Windermere, FL MLS# O6325457
$401,990
3

Beds

2.1

Baths

1,554

Sq.Ft.

8625 COVENTRY PARK WAY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 7482 BENTONSHIRE AVENUE Windermere, FL MLS# O6366524
  • Recently Listed with Virtual Tour
1 of 21
$399,900
3

Beds

2.1

Baths

1,428

Sq.Ft.

7482 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 14155 ANCILLA BOULEVARD Windermere, FL MLS# O6327707
$399,000
3

Beds

2.1

Baths

1,629

Sq.Ft.

14155 ANCILLA BOULEVARD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7777 MOSER AVENUE Windermere, FL MLS# O6367366
  • Recently Listed with Virtual Tour
1 of 32
$399,000
3

Beds

2.1

Baths

1,670

Sq.Ft.

7777 MOSER AVENUE

Windermere, FL

Courtesy of CREEGAN GROUP
View 8638 BROOKVALE DRIVE Windermere, FL MLS# O6360958
$395,000
3

Beds

2.1

Baths

1,520

Sq.Ft.

8638 BROOKVALE DRIVE

Windermere, FL

Courtesy of AK GLOBAL REALTY LLC
View 7711 FAIRGROVE AVENUE Windermere, FL MLS# O6352360
  • Virtual Tour
1 of 44
$389,900
3

Beds

2.1

Baths

1,680

Sq.Ft.

7711 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VOSS REALTY INC
View 5235 KEENES PHEASANT DRIVE Windermere, FL MLS# O6317036
$377,900
3

Beds

2.1

Baths

1,462

Sq.Ft.

5235 KEENES PHEASANT DRIVE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 14025 OASIS SPRINGS LANE 901 Windermere, FL MLS# O6311229
$375,000
3

Beds

2.1

Baths

1,786

Sq.Ft.

14025 OASIS SPRINGS LANE 901

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 7768 MOSER AVENUE Windermere, FL MLS# O6355727
  • Virtual Tour
1 of 7
$375,000
3

Beds

2.1

Baths

1,644

Sq.Ft.

7768 MOSER AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 12335 CRUXBURY DRIVE Windermere, FL MLS# O6311347
  • Virtual Tour
1 of 21
$369,999
2

Beds

2.1

Baths

1,510

Sq.Ft.

12335 CRUXBURY DRIVE

Windermere, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 12307 LANGSTAFF DRIVE Windermere, FL MLS# O6364588
  • Virtual Tour
1 of 36
$369,999
3

Beds

2.1

Baths

1,520

Sq.Ft.

12307 LANGSTAFF DRIVE

Windermere, FL

Courtesy of HOGAN REALTY GROUP INC
View 13907 ANCILLA BOULEVARD Windermere, FL MLS# O6365074
$360,000
2

Beds

2.0

Baths

1,155

Sq.Ft.

13907 ANCILLA BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III 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

286

Estimated median home price

$1,077,995
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

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 24
$400K - 500K 21
$500K - 600K 16
$600K - 700K 21
$700K - 800K 17
$800K - 900K 20
$900K - 1M 17
$1M - Max 150

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 227
Townhouse 37
Condo 9
Commercial 1
Rental 109
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/31/2025)

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 1/1/2026.