104 total properties
Did you mean the neighborhood Windermere?
View 13075 CALDERDALE AVENUE Windermere, FL MLS# O6372625
  • Recently Listed with Virtual Tour
1 of 19
$2,550
3

Beds

2.1

Baths

1,625

Sq.Ft.

13075 CALDERDALE AVENUE

Windermere, FL

Courtesy of BELLA TRAE REALTY
View 13040 OVERSTREET ROAD Windermere, FL MLS# V4946664
  • Recently Listed with Virtual Tour
1 of 45
$3,000
3

Beds

2.1

Baths

2,203

Sq.Ft.

13040 OVERSTREET ROAD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8264 MARITIME FLAG STREET 1419 Windermere, FL MLS# O6372117
  • Recently Listed with Virtual Tour
1 of 23
$2,095
2

Beds

2.0

Baths

1,161

Sq.Ft.

8264 MARITIME FLAG STREET 1419

Windermere, FL

Courtesy of RED DOOR INVESTMENT GRP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 12676 SALOMON COVE DRIVE Windermere, FL MLS# O6372332
  • Recently Listed with Virtual Tour
1 of 34
$4,150
6

Beds

4.0

Baths

3,667

Sq.Ft.

12676 SALOMON COVE DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 12921 CRAGSIDE LANE Windermere, FL MLS# O6372776
  • Recently Listed
1 of 7
$3,100
4

Beds

2.0

Baths

2,151

Sq.Ft.

12921 CRAGSIDE LANE

Windermere, FL

Courtesy of WINDERMERE INTERNATIONAL REALTY
View 3302 BUTLER BAY DRIVE N Windermere, FL MLS# O6371540
  • Recently Listed with Virtual Tour
1 of 22
$7,500
6

Beds

4.0

Baths

3,916

Sq.Ft.

3302 BUTLER BAY DRIVE N

Windermere, FL

Courtesy of JC FLORIDA REALTY LLC
View 8168 BOAT HOOK LOOP 202 Windermere, FL MLS# O6370921
  • Recently Listed with Virtual Tour
1 of 5
$1,775
2

Beds

2.0

Baths

1,161

Sq.Ft.

8168 BOAT HOOK LOOP 202

Windermere, FL

Courtesy of HAMPTON & HAMPTON MGMT LEASING
View 13154 KEGAN STREET Windermere, FL MLS# O6371410
  • Recently Listed with Virtual Tour
1 of 30
$3,600
5

Beds

4.1

Baths

2,961

Sq.Ft.

13154 KEGAN STREET

Windermere, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 2844 MIDSUMMER DRIVE Windermere, FL MLS# O6371115
$7,500
4

Beds

3.1

Baths

3,328

Sq.Ft.

2844 MIDSUMMER DRIVE

Windermere, FL

Courtesy of WINDERMERE COCOA BEACH CENTER
View 7307 ELLA LANE Windermere, FL MLS# O6370761
  • Recently Listed with Virtual Tour
1 of 53
$3,800
3

Beds

2.1

Baths

1,988

Sq.Ft.

7307 ELLA LANE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 8160 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6370560
  • Recently Listed with Virtual Tour
1 of 31
$2,875
3

Beds

2.1

Baths

2,009

Sq.Ft.

8160 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of GECKO REALTY, INC
View 9024 WOODBREEZE BOULEVARD Windermere, FL MLS# O6369946
  • Recently Listed with Virtual Tour
1 of 31
$3,100
4

Beds

2.1

Baths

2,020

Sq.Ft.

9024 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 13224 ORANGE ISLE DRIVE Windermere, FL MLS# O6370036
  • Recently Listed with Virtual Tour
1 of 40
$4,000
4

Beds

3.1

Baths

3,109

Sq.Ft.

13224 ORANGE ISLE DRIVE

Windermere, FL

Courtesy of RE REALTY
View 12337 VIA DERNA PLACE Windermere, FL MLS# O6369619
  • Recently Listed with Virtual Tour
1 of 23
$2,890
4

Beds

3.1

Baths

1,936

Sq.Ft.

12337 VIA DERNA PLACE

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 12880 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6369509
  • Recently Listed with Virtual Tour
1 of 42
$3,750
5

Beds

4.1

Baths

3,769

Sq.Ft.

12880 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 1351 GLENWICK DRIVE Windermere, FL MLS# O6369599
  • Recently Listed with Virtual Tour
1 of 18
$4,500
5

Beds

4.0

Baths

3,536

Sq.Ft.

1351 GLENWICK DRIVE

Windermere, FL

Courtesy of FLORIDA DREAMS REALTY GRP INC
View 8320 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5140587
  • Recently Listed with Virtual Tour
1 of 39
$2,887
4

Beds

2.1

Baths

1,766

Sq.Ft.

8320 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of TRANSCEND REALTY
View 7448 ELLA LANE Windermere, FL MLS# S5140669
  • Recently Listed with Virtual Tour
1 of 16
$3,500
4

Beds

2.1

Baths

2,623

Sq.Ft.

7448 ELLA LANE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8631 CRESCENDO AVENUE Windermere, FL MLS# O6368827
  • Recently Listed with Virtual Tour
1 of 18
$3,500
4

Beds

3.1

Baths

2,876

Sq.Ft.

8631 CRESCENDO AVENUE

Windermere, FL

Courtesy of REALTY HUB
View 12958 VENNETTA WAY Windermere, FL MLS# O6365367
$2,600
3

Beds

2.1

Baths

1,644

Sq.Ft.

12958 VENNETTA WAY

Windermere, FL

Courtesy of THE LISTING REAL ESTATE MANAGEMENT

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

273

Estimated median home price

$1,075,000
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 22
$400K - 500K 20
$500K - 600K 19
$600K - 700K 23
$700K - 800K 17
$800K - 900K 16
$900K - 1M 14
$1M - Max 142

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 217
Townhouse 35
Condo 7
Commercial 1
Rental 102
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 1/9/2026)

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 1/10/2026.