47 total properties
Did you mean the neighborhood Windermere?
View 12633 HADDON DRIVE Windermere, FL MLS# O6411199
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Sunday 5/31 1:00 PM - 3:00 PM
$650,000
5

Beds

3.1

Baths

3,000

Sq.Ft.

12633 HADDON DRIVE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 8715 QUIET MEADOWS TRAIL Windermere, FL MLS# O6410762
  • Recently Listed with Virtual Tour
1 of 51
$840,000
4

Beds

3.1

Baths

3,388

Sq.Ft.

8715 QUIET MEADOWS TRAIL

Windermere, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 9376 WOODBREEZE BOULEVARD Windermere, FL MLS# O6411270
  • Recently Listed with Virtual Tour
1 of 42
$675,000
4

Beds

2.1

Baths

2,026

Sq.Ft.

9376 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 8360 VIVARO ISLE WAY Windermere, FL MLS# S5150324
$690,000
4

Beds

3.0

Baths

2,224

Sq.Ft.

8360 VIVARO ISLE WAY

Windermere, FL

Courtesy of MD3 HOMES LLC
View 811 MAIN STREET Windermere, FL MLS# O6409463
  • Recently Listed with Virtual Tour
1 of 33
$649,999
2

Beds

1.1

Baths

1,398

Sq.Ft.

811 MAIN STREET

Windermere, FL

Courtesy of CAMERON REALTY GROUP LLC
View 4948 WISE BIRD DRIVE Windermere, FL MLS# O6405511
$679,000
3

Beds

2.0

Baths

1,979

Sq.Ft.

4948 WISE BIRD DRIVE

Windermere, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 6615 HELMSLEY CIRCLE Windermere, FL MLS# O6406997
$690,000
5

Beds

3.1

Baths

3,390

Sq.Ft.

6615 HELMSLEY CIRCLE

Windermere, FL

Courtesy of EXP REALTY LLC
View 4819 INDIAN DEER ROAD Windermere, FL MLS# O6403960
$669,900
4

Beds

4.0

Baths

3,049

Sq.Ft.

4819 INDIAN DEER ROAD

Windermere, FL

Courtesy of ENTERA REALTY LLC
View 7174 BEEK STREET Windermere, FL MLS# O6402279
  • Virtual Tour
1 of 47
$725,000
5

Beds

3.0

Baths

2,464

Sq.Ft.

7174 BEEK STREET

Windermere, FL

Courtesy of RE/MAX CENTRAL REALTY
View 13226 ZORI LANE Windermere, FL MLS# O6403132
  • Virtual Tour
1 of 41
$675,000
4

Beds

2.0

Baths

2,521

Sq.Ft.

13226 ZORI LANE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 1430 GLENWICK DRIVE Windermere, FL MLS# O6403052
$779,900
4

Beds

3.0

Baths

2,606

Sq.Ft.

1430 GLENWICK DRIVE

Windermere, FL

Courtesy of PREMIUM REAL ESTATE SERVICES
View 13836 BLUEBIRD POND ROAD Windermere, FL MLS# TB8502779
  • Virtual Tour
1 of 30
OPEN HOUSE: Sunday 5/31 12:00 PM - 4:00 PM
$698,000
3

Beds

2.0

Baths

2,108

Sq.Ft.

13836 BLUEBIRD POND ROAD

Windermere, FL

Courtesy of GETMOREOFFERS
View 13633 ANCILLA BOULEVARD Windermere, FL MLS# O6403031
$849,000
5

Beds

3.1

Baths

3,588

Sq.Ft.

13633 ANCILLA BOULEVARD

Windermere, FL

Courtesy of JUPITER PROPERTIES, INC
View 6956 TRELLIS VINE LOOP Windermere, FL MLS# O6401639
$650,000
5

Beds

4.0

Baths

3,015

Sq.Ft.

6956 TRELLIS VINE LOOP

Windermere, FL

Courtesy of EAST PEARL REALTY
View 1028 LASCALA DRIVE Windermere, FL MLS# O6400649
$749,000
4

Beds

2.1

Baths

2,208

Sq.Ft.

1028 LASCALA DRIVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786 Windermere, FL MLS# O6398784
$862,000
5

Beds

3.0

Baths

3,063

Sq.Ft.

1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13842 ORANGE CREST DRIVE Windermere, FL MLS# O6402132
$739,888
5

Beds

3.0

Baths

2,620

Sq.Ft.

13842 ORANGE CREST DRIVE

Windermere, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 825 OAKDALE STREET Windermere, FL MLS# O6396351
$792,500
3

Beds

2.0

Baths

1,664

Sq.Ft.

825 OAKDALE STREET

Windermere, FL

Courtesy of EXP REALTY LLC
View 4309 SALTMARSH SPARROW DRIVE Windermere, FL MLS# O6396295
  • Virtual Tour
1 of 55
OPEN HOUSE: Sunday 5/31 9:00 AM - 7:00 PM
$783,000
5

Beds

4.1

Baths

3,697

Sq.Ft.

4309 SALTMARSH SPARROW DRIVE

Windermere, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 9237 SABAL PALM CIRCLE Windermere, FL MLS# G5110005
$769,995
3

Beds

2.0

Baths

2,469

Sq.Ft.

9237 SABAL PALM CIRCLE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

351

Estimated median home price

$1,190,000
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 - 300K1
$300K - 400K22
$400K - 500K29
$500K - 600K33
$600K - 700K24
$700K - 800K18
$800K - 900K17
$900K - 1M16
$1M - Max191

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family286
Townhouse43
Condo7
Commercial1
Rental95
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/31/2026)

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 5/31/2026.