31 total properties
Did you mean the neighborhood Windermere?
View 6239 RYDAL COURT Windermere, FL MLS# O6435610
$1,495,000
5

Beds

4.1

Baths

4,238

Sq.Ft.

6239 RYDAL COURT

Windermere, FL

View 2031 WILLOW LAUREN LANE L Windermere, FL MLS# O6429898
  • Recently Listed with Virtual Tour
1 of 70
$1,249,000
5

Beds

4.1

Baths

3,664

Sq.Ft.

2031 WILLOW LAUREN LANE L

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17526 BLACK RAIL STREET Windermere, FL MLS# O6433513
  • Recently Listed with Virtual Tour
1 of 95
$1,500,000
5

Beds

4.0

Baths

3,656

Sq.Ft.

17526 BLACK RAIL STREET

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 212 W 1ST AVENUE Windermere, FL MLS# S5155372
  • Recently Listed with Virtual Tour
1 of 20
$1,650,000
4

Beds

2.0

Baths

2,627

Sq.Ft.

212 W 1ST AVENUE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 12676 SALOMON COVE DRIVE Windermere, FL MLS# O6429934
$1,300,000
6

Beds

4.0

Baths

3,667

Sq.Ft.

12676 SALOMON COVE DRIVE

Windermere, FL

View 14213 CREST PALM AVENUE Windermere, FL MLS# G5115749
$1,305,741
6

Beds

4.1

Baths

4,564

Sq.Ft.

14213 CREST PALM AVENUE

Windermere, FL

View 5746 OXFORD MOOR BOULEVARD Windermere, FL MLS# O6427113
$1,289,000
4

Beds

3.0

Baths

3,793

Sq.Ft.

5746 OXFORD MOOR BOULEVARD

Windermere, FL

View 12417 MONTALCINO CIRCLE Windermere, FL MLS# O6425494
$1,595,000
4

Beds

3.1

Baths

3,166

Sq.Ft.

12417 MONTALCINO CIRCLE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 20 OAKDALE STREET Windermere, FL MLS# O6421265
  • Virtual Tour
1 of 30
$1,499,000
3

Beds

2.1

Baths

2,188

Sq.Ft.

20 OAKDALE STREET

Windermere, FL

View 2617 BUTLER BAY DRIVE N Windermere, FL MLS# O6420023
$1,649,000
4

Beds

4.0

Baths

3,086

Sq.Ft.

2617 BUTLER BAY DRIVE N

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 6124 FOXFIELD COURT Windermere, FL MLS# O6419393
$1,250,000
4

Beds

3.0

Baths

2,887

Sq.Ft.

6124 FOXFIELD COURT

Windermere, FL

View 11027 HAWKSHEAD COURT Windermere, FL MLS# O6417606
$1,569,000
5

Beds

3.1

Baths

3,486

Sq.Ft.

11027 HAWKSHEAD COURT

Windermere, FL

View 11832 WATERSTONE LOOP DRIVE Windermere, FL MLS# O6415932
$1,575,000
4

Beds

4.1

Baths

3,396

Sq.Ft.

11832 WATERSTONE LOOP DRIVE

Windermere, FL

View 5741 OXFORD MOOR BOULEVARD Windermere, FL MLS# O6416690
$1,550,000
6

Beds

4.1

Baths

4,525

Sq.Ft.

5741 OXFORD MOOR BOULEVARD

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 11768 HAMPSTEAD STREET Windermere, FL MLS# O6414500
$1,318,000
6

Beds

4.0

Baths

3,900

Sq.Ft.

11768 HAMPSTEAD STREET

Windermere, FL

Courtesy of COMPASS FLORIDA, LLC
View 11035 SCHOONER WAY Windermere, FL MLS# O6413965
$1,500,000
4

Beds

3.0

Baths

3,517

Sq.Ft.

11035 SCHOONER WAY

Windermere, FL

View 11524 CLAYMONT CIRCLE Windermere, FL MLS# O6410754
$1,288,999
5

Beds

4.0

Baths

3,358

Sq.Ft.

11524 CLAYMONT CIRCLE

Windermere, FL

View 1700 LAKE ROBERTS COURT Windermere, FL MLS# O6410847
$1,350,000
5

Beds

4.0

Baths

3,929

Sq.Ft.

1700 LAKE ROBERTS COURT

Windermere, FL

View 9527 QUEENSBURY COURT Windermere, FL MLS# O6408997
$1,425,000
5

Beds

4.2

Baths

5,378

Sq.Ft.

9527 QUEENSBURY COURT

Windermere, FL

View 9548 CROWN PRINCE LANE Windermere, FL MLS# O6407352
$1,450,000
4

Beds

4.0

Baths

3,997

Sq.Ft.

9548 CROWN PRINCE LANE

Windermere, FL

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

324

Estimated median home price

$984,750
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 - 200K1
$200K - 300K2
$300K - 400K21
$400K - 500K31
$500K - 600K32
$600K - 700K31
$700K - 800K19
$800K - 900K15
$900K - 1M13
$1M - Max159

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family251
Townhouse46
Condo10
Commercial1
Rental83
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 8/27/2026)

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 8/28/2026.