114 total properties
Did you mean the neighborhood Windermere?
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
  • Recently Listed
1 of 32
OPEN HOUSE: Sunday 2/8 12:00 PM - 3:00 PM
$469,999
3

Beds

2.1

Baths

2,002

Sq.Ft.

13733 BRESSLER ALLEY

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 12944 GARRIDAN AVENUE Windermere, FL MLS# O6380101
  • Recently Listed with Virtual Tour
1 of 39
$419,000
3

Beds

2.1

Baths

1,583

Sq.Ft.

12944 GARRIDAN AVENUE

Windermere, FL

Courtesy of 407 PROPERTIES
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
  • Recently Listed with Virtual Tour
1 of 74
$799,000
4

Beds

4.0

Baths

2,623

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
  • Recently Listed with Virtual Tour
1 of 56
OPEN HOUSE: Saturday 2/7 1:00 PM - 3:00 PM
$595,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6382 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 8168 BOAT HOOK LOOP 207 Windermere, FL MLS# O6378432
  • Recently Listed with Virtual Tour
1 of 21
$324,500
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 207

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 5018 RIVER GEM AVENUE Windermere, FL MLS# TB8469061
  • Recently Listed with Virtual Tour
1 of 46
$785,000
3

Beds

2.1

Baths

2,379

Sq.Ft.

5018 RIVER GEM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA
View 13912 DARCHANCE ROAD Windermere, FL MLS# O6377606
  • Virtual Tour
1 of 49
OPEN HOUSE: Saturday 2/7 1:00 PM - 4:00 PM
$709,999
4

Beds

3.1

Baths

2,699

Sq.Ft.

13912 DARCHANCE ROAD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 9047 REFLECTION POINTE DRIVE Windermere, FL MLS# O6378672
  • Recently Listed with Virtual Tour
1 of 57
$755,000
4

Beds

4.0

Baths

3,019

Sq.Ft.

9047 REFLECTION POINTE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
  • Recently Listed with Virtual Tour
1 of 29
$699,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6376756
  • Recently Listed with Virtual Tour
1 of 29
$799,000
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of U S GLORY REALTY
View 415 E 6TH AVENUE Windermere, FL MLS# O6376614
  • Virtual Tour
1 of 47
$699,815
3

Beds

2.0

Baths

1,784

Sq.Ft.

415 E 6TH AVENUE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 5463 GEMGOLD COURT Windermere, FL MLS# O6375567
$599,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

5463 GEMGOLD COURT

Windermere, FL

Courtesy of INFINITY REALTY GROUP LLC
View 12214 LANGSTAFF DRIVE Windermere, FL MLS# O6376431
  • Recently Listed with Virtual Tour
1 of 15
$389,000
3

Beds

2.1

Baths

1,545

Sq.Ft.

12214 LANGSTAFF DRIVE

Windermere, FL

Courtesy of PREMIUM REALTY GROUP USA
View 8650 ABBOTSBURY DRIVE Windermere, FL MLS# O6376488
  • Recently Listed with Virtual Tour
1 of 47
$595,000
4

Beds

3.1

Baths

2,628

Sq.Ft.

8650 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of THE AGENCY FL
View 6876 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6373037
  • Recently Listed with Virtual Tour
1 of 48
$678,990
4

Beds

2.1

Baths

2,781

Sq.Ft.

6876 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 6638 BRIDGEWATER VILLAGE ROAD Windermere, FL MLS# O6374429
  • Recently Listed with Virtual Tour
1 of 40
OPEN HOUSE: Saturday 2/7 1:00 PM - 3:00 PM
$664,900
4

Beds

2.1

Baths

2,908

Sq.Ft.

6638 BRIDGEWATER VILLAGE ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7451 FAIRGROVE AVENUE Windermere, FL MLS# O6375170
  • Recently Listed with Virtual Tour
1 of 46
$580,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

7451 FAIRGROVE AVENUE

Windermere, FL

Courtesy of TALENT REALTY SOLUTIONS
View 8648 POWDER RIDGE TRAIL Windermere, FL MLS# O6373065
$528,000
3

Beds

2.1

Baths

1,876

Sq.Ft.

8648 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 7885 BERKSHIRE OAK ALLEY Windermere, FL MLS# O6374875
$579,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7885 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of U S GLORY REALTY
View 6841 HELMSLEY CIRCLE Windermere, FL MLS# O6372635
$650,000
4

Beds

3.0

Baths

2,371

Sq.Ft.

6841 HELMSLEY CIRCLE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE

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

287

Estimated median home price

$1,037,000
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 - 400K17
$400K - 500K21
$500K - 600K23
$600K - 700K31
$700K - 800K19
$800K - 900K17
$900K - 1M11
$1M - Max147

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family236
Townhouse29
Condo8
Commercial1
Rental100
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/6/2026)

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 2/7/2026.