88 total properties
Did you mean the neighborhood Windermere?
View 14217 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL MLS# O6396155
$600,000
4

Beds

3.0

Baths

2,419

Sq.Ft.

14217 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 13419 LEMON ORCHARD BEND Windermere, FL MLS# TB8528688
  • New Construction with Virtual Tour
1 of 21
$599,990
3

Beds

2.1

Baths

1,699

Sq.Ft.

13419 LEMON ORCHARD BEND

Windermere, FL

View 13231 ROXBORO ROAD Windermere, FL MLS# O6427997
  • Recently Listed
1 of 42
$599,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

13231 ROXBORO ROAD

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 9011 CHAPMAN OAK COURT Windermere, FL MLS# S5148031
  • Adult Community with Virtual Tour
1 of 30
$599,000
4

Beds

2.0

Baths

2,050

Sq.Ft.

9011 CHAPMAN OAK COURT

Windermere, FL

View 13403 RIGGS WAY Windermere, FL MLS# O6426117
  • Virtual Tour
1 of 47
$599,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13403 RIGGS WAY

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 1516 HEMPEL AVENUE Windermere, FL MLS# O6342593
$595,000
Studio

Beds

0.0

Baths

1516 HEMPEL AVENUE

Windermere, FL

View 12789 BOSWORTH AVENUE Windermere, FL MLS# O6423464
  • Recently Listed with Virtual Tour
1 of 32
$585,000
3

Beds

2.0

Baths

1,710

Sq.Ft.

12789 BOSWORTH AVENUE

Windermere, FL

View 7011 NOBLETON DRIVE Windermere, FL MLS# O6412101
$580,000
4

Beds

2.1

Baths

2,460

Sq.Ft.

7011 NOBLETON DRIVE

Windermere, FL

Courtesy of KARDOSH REALTY
View 5577 LEMON ORCHARD BEND Windermere, FL MLS# TB8534803
$579,857
3

Beds

2.1

Baths

1,699

Sq.Ft.

5577 LEMON ORCHARD BEND

Windermere, FL

View 9802 6TH STREET Windermere, FL MLS# O6349678
$575,000
Studio

Beds

0.0

Baths

9802 6TH STREET

Windermere, FL

View 5032 BEACH RIVER ROAD Windermere, FL MLS# O6418594
$569,000
4

Beds

2.1

Baths

2,306

Sq.Ft.

5032 BEACH RIVER ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 13219 CHARFIELD STREET Windermere, FL MLS# O6420991
$565,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13219 CHARFIELD STREET

Windermere, FL

View 13411 LEMON ORCHARD BEND Windermere, FL MLS# TB8493546
  • New Construction with Virtual Tour
1 of 20
$561,738
3

Beds

2.1

Baths

1,649

Sq.Ft.

13411 LEMON ORCHARD BEND

Windermere, FL

View 8225 BRYCE CANYON AVENUE Windermere, FL MLS# O6371960
$560,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

8225 BRYCE CANYON AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13137 PENSHURST LANE Windermere, FL MLS# O6421270
$560,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13137 PENSHURST LANE

Windermere, FL

View 4627 BLUE MAJOR DRIVE Windermere, FL MLS# O6397778
$559,000
4

Beds

3.0

Baths

2,411

Sq.Ft.

4627 BLUE MAJOR DRIVE

Windermere, FL

View 11468 MISTY OAK ALLEY Windermere, FL MLS# O6425336
$558,900
3

Beds

2.1

Baths

2,014

Sq.Ft.

11468 MISTY OAK ALLEY

Windermere, FL

View 9319 WOODBREEZE BOULEVARD Windermere, FL MLS# O6384930
$554,555
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13330 LONGACRE DRIVE Windermere, FL MLS# O6418405
$550,000
3

Beds

2.1

Baths

2,306

Sq.Ft.

13330 LONGACRE DRIVE

Windermere, FL

Courtesy of SUNSTAR REALTY FL INC
View 1661 ROBERTS LANDING ROAD Windermere, FL MLS# O6407725
$549,900
Studio

Beds

0.0

Baths

1661 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

331

Estimated median home price

$995,000
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 - 400K20
$400K - 500K36
$500K - 600K30
$600K - 700K32
$700K - 800K21
$800K - 900K13
$900K - 1M12
$1M - Max164

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family258
Townhouse45
Condo11
Commercial1
Rental71
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 8/6/2026)

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 8/7/2026.