320 total properties
Did you mean the neighborhood Windermere?
View 1924 DOWN HOLLOW LANE Windermere, FL MLS# O6398100
$1,680,000
3

Beds

2.1

Baths

1,962

Sq.Ft.

1924 DOWN HOLLOW LANE

Windermere, FL

View 212 W 1ST AVENUE Windermere, FL MLS# S5147532
  • Virtual Tour
1 of 21
$1,650,000
Studio

Beds

0.0

Baths

212 W 1ST AVENUE

Windermere, FL

View 7503 LAKE ALBERT DR Windermere, FL MLS# S5149564
$1,650,000
5

Beds

5.0

Baths

4,329

Sq.Ft.

7503 LAKE ALBERT DR

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 11923 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6311003
$1,630,000
3

Beds

2.0

Baths

2,238

Sq.Ft.

11923 LAKE BUTLER BOULEVARD

Windermere, FL

View 11832 WATERSTONE LOOP DRIVE Windermere, FL MLS# O6415932
$1,595,000
4

Beds

4.1

Baths

3,396

Sq.Ft.

11832 WATERSTONE LOOP DRIVE

Windermere, FL

View 6533 CARTMEL LN Windermere, FL MLS# O6425396
  • Recently Listed with Virtual Tour
1 of 34
$1,595,000
5

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LN

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 12417 MONTALCINO CIRCLE Windermere, FL MLS# O6425494
  • Recently Listed with Virtual Tour
1 of 100
$1,595,000
4

Beds

3.1

Baths

3,166

Sq.Ft.

12417 MONTALCINO CIRCLE

Windermere, FL

View 13124 FILLY COURT Windermere, FL MLS# O6303140
  • Virtual Tour
1 of 51
OPEN HOUSE: Saturday 7/25 12:00 PM - 3:00 PM
$1,575,000
5

Beds

3.0

Baths

3,300

Sq.Ft.

13124 FILLY COURT

Windermere, FL

View 33 MAIN STREET Windermere, FL MLS# O6406887
$1,575,000
4

Beds

2.0

Baths

2,130

Sq.Ft.

33 MAIN STREET

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 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 10948 DOWN PARK LANE Windermere, FL MLS# O6389820
$1,545,000
Studio

Beds

0.0

Baths

10948 DOWN PARK LANE

Windermere, FL

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 9527 QUEENSBURY COURT Windermere, FL MLS# O6408997
$1,499,900
5

Beds

4.2

Baths

5,378

Sq.Ft.

9527 QUEENSBURY COURT

Windermere, FL

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 11339 CAMDEN PARK DRIVE Windermere, FL MLS# O6388110
$1,490,000
5

Beds

4.0

Baths

3,492

Sq.Ft.

11339 CAMDEN PARK DRIVE

Windermere, FL

View 12718 WINDERMERE ISLES PLACE Windermere, FL MLS# O6399958
$1,480,000
5

Beds

4.0

Baths

3,487

Sq.Ft.

12718 WINDERMERE ISLES PLACE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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

View 11015 HAWKSHEAD COURT Windermere, FL MLS# O6405977
$1,450,000
5

Beds

4.1

Baths

3,868

Sq.Ft.

11015 HAWKSHEAD COURT

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

351

Estimated median home price

$1,058,989
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 - 300K3
$300K - 400K19
$400K - 500K37
$500K - 600K31
$600K - 700K31
$700K - 800K20
$800K - 900K16
$900K - 1M14
$1M - Max180

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family280
Townhouse44
Condo10
Commercial1
Rental85
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/24/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 7/25/2026.