30 total properties
Did you mean the neighborhood Windermere?
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 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 6241 BLAKEFORD DRIVE Windermere, FL MLS# O6417788
  • Recently Listed with Virtual Tour
1 of 59
$1,795,000
4

Beds

4.0

Baths

3,556

Sq.Ft.

6241 BLAKEFORD DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 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
$1,595,000
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 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 2503 BUTLER BAY DRIVE N Windermere, FL MLS# O6413242
$1,750,000
4

Beds

3.0

Baths

3,297

Sq.Ft.

2503 BUTLER BAY DRIVE N

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 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 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 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

View 5421 TILDENS GROVE BOULEVARD Windermere, FL MLS# O6402594
$1,999,900
6

Beds

4.1

Baths

5,922

Sq.Ft.

5421 TILDENS GROVE BOULEVARD

Windermere, FL

Courtesy of DERENTHAL REALTY
View 6036 GREATWATER DR Windermere, FL MLS# O6400277
$1,999,999
4

Beds

4.1

Baths

4,013

Sq.Ft.

6036 GREATWATER DR

Windermere, FL

View 11051 HAWKSHEAD COURT Windermere, FL MLS# O6400963
$1,825,000
5

Beds

4.2

Baths

3,728

Sq.Ft.

11051 HAWKSHEAD COURT

Windermere, FL

Courtesy of REAL BROKER, LLC
View 11449 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6399319
$1,680,000
5

Beds

3.2

Baths

4,648

Sq.Ft.

11449 LAKE BUTLER BOULEVARD

Windermere, FL

View 11226 MACAW COURT Windermere, FL MLS# O6393210
  • Virtual Tour
1 of 77
$1,825,000
4

Beds

4.1

Baths

4,549

Sq.Ft.

11226 MACAW COURT

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

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

345

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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K3
$300K - 400K18
$400K - 500K37
$500K - 600K31
$600K - 700K30
$700K - 800K17
$800K - 900K16
$900K - 1M14
$1M - Max179

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family275
Townhouse43
Condo10
Commercial1
Rental87
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/23/2026)

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 7/24/2026.