290 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 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

The time to sell is now! THE TIME TO SELL IS NOW!
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

View 12411 MONTALCINO CIRCLE Windermere, FL MLS# O6400067
$1,439,000
4

Beds

4.1

Baths

3,399

Sq.Ft.

12411 MONTALCINO CIRCLE

Windermere, FL

View 11537 CLAYMONT CIR Windermere, FL MLS# O6395210
$1,400,000
5

Beds

4.0

Baths

3,164

Sq.Ft.

11537 CLAYMONT CIR

Windermere, FL

View 1700 LAKE ROBERTS COURT Windermere, FL MLS# O6410847
  • Virtual Tour
1 of 47
OPEN HOUSE: Saturday 7/25 12:00 PM - 2:00 PM
$1,400,000
5

Beds

4.0

Baths

3,929

Sq.Ft.

1700 LAKE ROBERTS COURT

Windermere, FL

View 9119 BALMORAL MEWS SQ Windermere, FL MLS# S5146725
$1,399,000
4

Beds

4.0

Baths

4,052

Sq.Ft.

9119 BALMORAL MEWS SQ

Windermere, FL

View 8463 TIBET BUTLER DR Windermere, FL MLS# O6417589
$1,399,000
4

Beds

4.2

Baths

3,786

Sq.Ft.

8463 TIBET BUTLER DR

Windermere, FL

View 13596 GORGONA ISLE DRIVE Windermere, FL MLS# O6374555
$1,396,000
6

Beds

4.1

Baths

3,794

Sq.Ft.

13596 GORGONA ISLE DRIVE

Windermere, FL

View 2014 DOWN WOODS LANE Windermere, FL MLS# O6413750
$1,390,000
4

Beds

3.1

Baths

3,344

Sq.Ft.

2014 DOWN WOODS 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

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.

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 7/23/2026.