42 total properties
Did you mean the neighborhood Windermere?
View 7432 LEIGHSIDE DRIVE Windermere, FL MLS# O6383362
  • Recently Listed with Virtual Tour
1 of 36
$475,000
4

Beds

2.1

Baths

1,898

Sq.Ft.

7432 LEIGHSIDE DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 12879 EMERSONDALE AVENUE Windermere, FL MLS# O6383280
  • Recently Listed
1 of 23
$399,000
3

Beds

2.1

Baths

1,565

Sq.Ft.

12879 EMERSONDALE AVENUE

Windermere, FL

Courtesy of UNIONE REALTY INC
View 8162 SERENITY SPRING DR. Windermere, FL MLS# O6382279
$395,000
4

Beds

2.1

Baths

2,028

Sq.Ft.

8162 SERENITY SPRING DR.

Windermere, FL

Courtesy of WOODSTONE INVESTMENTS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 11434 JASPER KAY TERRACE 1120 Windermere, FL MLS# O6382035
  • Recently Listed with Virtual Tour
1 of 22
$325,000
3

Beds

2.0

Baths

1,332

Sq.Ft.

11434 JASPER KAY TERRACE 1120

Windermere, FL

Courtesy of REALTY ONE GROUP MVP
View 11408 CENTER LAKE DRIVE Windermere, FL MLS# O6381662
  • Recently Listed with Virtual Tour
1 of 39
$460,000
3

Beds

2.1

Baths

1,910

Sq.Ft.

11408 CENTER LAKE DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 13712 SUMMERPORT VILLAGE PARKWAY Windermere, FL MLS# S5143431
  • Recently Listed with Virtual Tour
1 of 64
$444,900
3

Beds

2.1

Baths

1,997

Sq.Ft.

13712 SUMMERPORT VILLAGE PARKWAY

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 12840 CALDERDALE AVENUE Windermere, FL MLS# O6381937
$435,000
4

Beds

3.1

Baths

1,905

Sq.Ft.

12840 CALDERDALE AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
  • Recently Listed
1 of 32
$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
  • 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 7422 BENTONSHIRE AVENUE Windermere, FL MLS# O6380109
  • Recently Listed with Virtual Tour
1 of 28
$349,000
2

Beds

2.1

Baths

1,360

Sq.Ft.

7422 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 8168 BOAT HOOK LOOP 207/714 Windermere, FL MLS# O6378432
$324,500
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 207/714

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 12214 LANGSTAFF DRIVE Windermere, FL MLS# O6376431
  • 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 13366 ABUELA ALLEY Windermere, FL MLS# O6374298
  • Virtual Tour
1 of 35
$444,000
3

Beds

2.1

Baths

1,589

Sq.Ft.

13366 ABUELA ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 8180 BOAT HOOK LOOP 108/301 Windermere, FL MLS# TB8465266
$333,333
3

Beds

2.0

Baths

1,442

Sq.Ft.

8180 BOAT HOOK LOOP 108/301

Windermere, FL

Courtesy of EXP REALTY LLC
View 13369 GORGONA ISLE DRIVE Windermere, FL MLS# O6373676
$459,900
3

Beds

2.1

Baths

1,767

Sq.Ft.

13369 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 12305 VIA DERNA PLACE Windermere, FL MLS# O6374964
  • Virtual Tour
1 of 24
$470,000
3

Beds

3.0

Baths

1,891

Sq.Ft.

12305 VIA DERNA PLACE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 7712 MOSER AVENUE Windermere, FL MLS# A4676630
  • Virtual Tour
1 of 30
$399,000
3

Beds

2.1

Baths

1,680

Sq.Ft.

7712 MOSER AVENUE

Windermere, FL

Courtesy of SUNCOAST REALTY SOLUTIONS, LLC
View 13285 GORGONA ISLE DRIVE Windermere, FL MLS# O6370659
  • Adult Community
1 of 45
$415,000
3

Beds

2.1

Baths

1,547

Sq.Ft.

13285 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of REALTY HUB
View 11209 GRANDER DRIVE Windermere, FL MLS# O6369918
  • Virtual Tour
1 of 35
$434,000
3

Beds

2.1

Baths

1,893

Sq.Ft.

11209 GRANDER DRIVE

Windermere, FL

Courtesy of MARTI PURDY PROPERTIES INC
View 6310 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6368983
$490,000
3

Beds

2.1

Baths

1,977

Sq.Ft.

6310 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of JOY ESTATE ENTERPRISE 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

299

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

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 19
$400K - 500K 22
$500K - 600K 27
$600K - 700K 25
$700K - 800K 24
$800K - 900K 20
$900K - 1M 10
$1M - Max 152

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 246
Townhouse 32
Condo 7
Commercial 1
Rental 103
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 2/24/2026)

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 2/24/2026.