50 total properties
Did you mean the neighborhood Windermere?
View 8146 JAILENE DRIVE Windermere, FL MLS# O6420838
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Sunday 7/5 11:00 AM - 4:00 PM
$574,900
3

Beds

2.0

Baths

2,099

Sq.Ft.

8146 JAILENE DRIVE

Windermere, FL

View 13137 PENSHURST LANE Windermere, FL MLS# O6421270
  • Recently Listed with Virtual Tour
1 of 46
$560,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13137 PENSHURST LANE

Windermere, FL

View 12580 CRAGSIDE LANE Windermere, FL MLS# O6418877
  • Recently Listed with Virtual Tour
1 of 62
$624,000
4

Beds

2.1

Baths

2,776

Sq.Ft.

12580 CRAGSIDE LANE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 5032 BEACH RIVER ROAD Windermere, FL MLS# O6418594
  • Recently Listed with Virtual Tour
1 of 29
$569,000
4

Beds

3.1

Baths

2,306

Sq.Ft.

5032 BEACH RIVER ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 13424 HOPKINTON CT Windermere, FL MLS# O6419100
  • Recently Listed with Virtual Tour
1 of 8
$549,999
4

Beds

3.0

Baths

2,190

Sq.Ft.

13424 HOPKINTON CT

Windermere, FL

View 13330 LONGACRE DRIVE Windermere, FL MLS# O6418405
  • Recently Listed with Virtual Tour
1 of 17
$550,000
3

Beds

2.1

Baths

2,306

Sq.Ft.

13330 LONGACRE DRIVE

Windermere, FL

Courtesy of SUNSTAR REALTY FL INC
View 6644 SAWYER SHORES LANE Windermere, FL MLS# O6417657
$600,000
Studio

Beds

0.0

Baths

6644 SAWYER SHORES LANE

Windermere, FL

View 13407 LEMON ORCHARD BEND Windermere, FL MLS# TB8519889
  • Recently Listed with Virtual Tour
1 of 18
$648,683
3

Beds

2.1

Baths

1,714

Sq.Ft.

13407 LEMON ORCHARD BEND

Windermere, FL

View 6648 HELSTON LANE Windermere, FL MLS# O6413354
  • Virtual Tour
1 of 47
$665,000
4

Beds

3.1

Baths

3,072

Sq.Ft.

6648 HELSTON LANE

Windermere, FL

View 8662 ABBOTSBURY DRIVE Windermere, FL MLS# O6416099
  • Recently Listed with Virtual Tour
1 of 38
$525,000
3

Beds

2.0

Baths

1,877

Sq.Ft.

8662 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 9110 PALM TREE DRIVE Windermere, FL MLS# O6414631
  • Recently Listed with Virtual Tour
1 of 30
$650,000
3

Beds

2.0

Baths

1,819

Sq.Ft.

9110 PALM TREE DRIVE

Windermere, FL

View 6558 HELMSLEY CIRCLE Windermere, FL MLS# S5151342
  • Recently Listed with Virtual Tour
1 of 56
OPEN HOUSE: Sunday 7/5 12:00 PM - 2:30 PM
$630,000
4

Beds

3.0

Baths

2,575

Sq.Ft.

6558 HELMSLEY CIRCLE

Windermere, FL

View 13324 LONGACRE DRIVE Windermere, FL MLS# S5151263
$510,000
3

Beds

2.0

Baths

2,058

Sq.Ft.

13324 LONGACRE DRIVE

Windermere, FL

View 6601 DUNCASTER STREET Windermere, FL MLS# O6416272
  • Recently Listed with Virtual Tour
1 of 65
$627,900
4

Beds

3.0

Baths

3,001

Sq.Ft.

6601 DUNCASTER STREET

Windermere, FL

View 13786 SUMMER HARBOR COURT Windermere, FL MLS# O6414239
$625,000
4

Beds

2.1

Baths

2,236

Sq.Ft.

13786 SUMMER HARBOR COURT

Windermere, FL

View 12826 WOODMERE CLOSE DR Windermere, FL MLS# O6412588
$665,000
4

Beds

3.0

Baths

2,214

Sq.Ft.

12826 WOODMERE CLOSE DR

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 11822 SILVERLAKE PARK DRIVE Windermere, FL MLS# O6409301
$495,000
3

Beds

2.1

Baths

1,829

Sq.Ft.

11822 SILVERLAKE PARK DRIVE

Windermere, FL

Courtesy of REDFIN CORPORATION
View 6412 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6412095
$550,000
3

Beds

2.1

Baths

1,984

Sq.Ft.

6412 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of URBAN-O REAL ESTATE SOLUTIONS
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 13936 EDEN ISLE BOULEVARD Windermere, FL MLS# S5150801
$655,000
4

Beds

3.1

Baths

2,675

Sq.Ft.

13936 EDEN ISLE BOULEVARD

Windermere, FL

Courtesy of TRANSCEND REALTY

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

364

Estimated median home price

$1,110,000
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 - 600K32
$600K - 700K27
$700K - 800K19
$800K - 900K21
$900K - 1M15
$1M - Max191

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family288
Townhouse51
Condo7
Commercial1
Rental99
Lots and Land17
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/1/2026)

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 7/2/2026.