52 total properties
Did you mean the neighborhood Windermere?
View 8259 MARITIME FLAG STREET 4 Windermere, FL MLS# O6329585
$320,000
3

Beds

2.1

Baths

1,460

Sq.Ft.

8259 MARITIME FLAG STREET 4

Windermere, FL

Courtesy of REAL BROKER, LLC
View 10750 REAMS ROAD Windermere, FL MLS# O6326716
  • Virtual Tour
1 of 46
$500,000
3

Beds

2.1

Baths

1,826

Sq.Ft.

10750 REAMS ROAD

Windermere, FL

Courtesy of EXECUTIVE PROPERTIES
View 11322 RAPALLO LANE Windermere, FL MLS# O6315831
$550,000
4

Beds

2.0

Baths

2,159

Sq.Ft.

11322 RAPALLO LANE

Windermere, FL

Courtesy of REDFIN CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
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 12335 CRUXBURY DRIVE Windermere, FL MLS# O6311347
$369,999
2

Beds

2.1

Baths

1,510

Sq.Ft.

12335 CRUXBURY DRIVE

Windermere, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 14242 DESERT HAVEN STREET GE Windermere, FL MLS# O6319072
$330,000
3

Beds

2.1

Baths

1,534

Sq.Ft.

14242 DESERT HAVEN STREET GE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 7462 BENTONSHIRE AVE Windermere, FL MLS# O6317645
$359,000
3

Beds

2.1

Baths

1,480

Sq.Ft.

7462 BENTONSHIRE AVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 14025 OASIS SPRINGS LANE 901 Windermere, FL MLS# O6311229
$365,000
3

Beds

2.1

Baths

1,786

Sq.Ft.

14025 OASIS SPRINGS LANE 901

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
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 7349 ELLA LANE Windermere, FL MLS# O6304618
  • Virtual Tour
1 of 11
$549,900
4

Beds

3.1

Baths

2,461

Sq.Ft.

7349 ELLA LANE

Windermere, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC
View 12930 VENNETTA WAY Windermere, FL MLS# O6301208
  • Virtual Tour
1 of 38
OPEN HOUSE: Saturday 1/17 11:00 AM - 1:00 PM
$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

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

277

Estimated median home price

$1,045,000
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 - 300K0
$300K - 400K22
$400K - 500K21
$500K - 600K20
$600K - 700K24
$700K - 800K19
$800K - 900K15
$900K - 1M14
$1M - Max142

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family220
Townhouse36
Condo7
Commercial1
Rental104
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 1/11/2026)

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 1/13/2026.