95 total properties
Did you mean the neighborhood Windermere?
View 935 LASCALA DRIVE Windermere, FL MLS# O6391352
  • Recently Listed with Virtual Tour
1 of 30
$2,495
3

Beds

2.0

Baths

1,601

Sq.Ft.

935 LASCALA DRIVE

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 4818 BREEZY PALMS COURT Windermere, FL MLS# O6391402
  • Recently Listed with Virtual Tour
1 of 27
$3,049
3

Beds

2.0

Baths

1,492

Sq.Ft.

4818 BREEZY PALMS COURT

Windermere, FL

Courtesy of 407 PROPERTIES
View 6615 HELMSLEY CIRCLE Windermere, FL MLS# G5109789
  • Recently Listed
1 of 42
$4,500
4

Beds

3.1

Baths

3,390

Sq.Ft.

6615 HELMSLEY CIRCLE

Windermere, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8476 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5145826
  • Recently Listed with Virtual Tour
1 of 23
$3,100
3

Beds

2.1

Baths

1,700

Sq.Ft.

8476 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 8921 NEWMARKET DRIVE Windermere, FL MLS# O6390585
  • Recently Listed with Virtual Tour
1 of 8
$2,350
3

Beds

2.1

Baths

1,429

Sq.Ft.

8921 NEWMARKET DRIVE

Windermere, FL

Courtesy of GOLDEN PACIFIC REALTY INC
View 8913 MATRIARCA ALY Windermere, FL MLS# S5145953
  • Recently Listed
1 of 30
$2,800
3

Beds

2.1

Baths

1,556

Sq.Ft.

8913 MATRIARCA ALY

Windermere, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 7307 PENKRIDGE LANE Windermere, FL MLS# O6384396
  • Recently Listed with Virtual Tour
1 of 38
$2,900
4

Beds

2.1

Baths

1,997

Sq.Ft.

7307 PENKRIDGE LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 8326 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5145711
  • Recently Listed with Virtual Tour
1 of 32
$2,697
3

Beds

2.1

Baths

1,631

Sq.Ft.

8326 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of TRANSCEND REALTY
View 7135 THICKET BRANCH ALLEY Windermere, FL MLS# O6389351
  • Recently Listed with Virtual Tour
1 of 16
$2,600
3

Beds

2.1

Baths

1,569

Sq.Ft.

7135 THICKET BRANCH ALLEY

Windermere, FL

Courtesy of JULIAN PROPERTIES, INC.
View 7349 ELLA LANE Windermere, FL MLS# O6389749
  • Recently Listed with Virtual Tour
1 of 9
$2,600
4

Beds

3.1

Baths

2,461

Sq.Ft.

7349 ELLA LANE

Windermere, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC
View 11213 CAMDEN PARK DRIVE Windermere, FL MLS# O6389289
  • Recently Listed with Virtual Tour
1 of 100
$8,750
4

Beds

3.1

Baths

2,902

Sq.Ft.

11213 CAMDEN PARK DRIVE

Windermere, FL

Courtesy of S2J REALTY, LLC
View 13643 LAKE CAWOOD DRIVE Windermere, FL MLS# O6389529
  • Recently Listed with Virtual Tour
1 of 78
$12,800
8

Beds

7.1

Baths

8,203

Sq.Ft.

13643 LAKE CAWOOD DRIVE

Windermere, FL

Courtesy of JWJ REALTY LLC
View 11434 JASPER KAY TERRACE 206 Windermere, FL MLS# O6390889
  • Recently Listed with Virtual Tour
1 of 45
$2,350
3

Beds

2.0

Baths

1,455

Sq.Ft.

11434 JASPER KAY TERRACE 206

Windermere, FL

Courtesy of MNT INTERNATIONAL
View 11456 CENTER LAKE DRIVE Windermere, FL MLS# O6388958
$2,550
3

Beds

2.1

Baths

1,881

Sq.Ft.

11456 CENTER LAKE DRIVE

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 8408 ABBOTSBURY DRIVE Windermere, FL MLS# O6388448
  • Recently Listed with Virtual Tour
1 of 9
$2,800
4

Beds

3.0

Baths

2,343

Sq.Ft.

8408 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 14200 OASIS COVE BOULEVARD 3301 Windermere, FL MLS# S5145300
  • Recently Listed with Virtual Tour
1 of 48
$3,000
3

Beds

2.1

Baths

1,638

Sq.Ft.

14200 OASIS COVE BOULEVARD 3301

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 12761 BIDEFORD AVENUE Windermere, FL MLS# O6387477
  • Recently Listed with Virtual Tour
1 of 37
$3,500
4

Beds

2.1

Baths

3,011

Sq.Ft.

12761 BIDEFORD AVENUE

Windermere, FL

Courtesy of SHINING OAK REALTY
View 1602 ROBERTS LANDING ROAD Windermere, FL MLS# O6387865
  • Recently Listed with Virtual Tour
1 of 13
$3,000
4

Beds

2.0

Baths

2,352

Sq.Ft.

1602 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of ASA FLORIDA PROPERTIES INC
View 8532 BOWDEN WAY Windermere, FL MLS# O6380872
$9,800
4

Beds

4.0

Baths

3,885

Sq.Ft.

8532 BOWDEN WAY

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8973 MATRIARCA ALLEY Windermere, FL MLS# O6387553
  • Recently Listed with Virtual Tour
1 of 29
$2,750
3

Beds

2.1

Baths

1,690

Sq.Ft.

8973 MATRIARCA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA

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

315

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 - 300K0
$300K - 400K15
$400K - 500K24
$500K - 600K32
$600K - 700K24
$700K - 800K25
$800K - 900K20
$900K - 1M15
$1M - Max160

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family263
Townhouse35
Condo3
Commercial1
Rental94
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/18/2026)

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 3/19/2026.