50 total properties
Did you mean the neighborhood Windermere?
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
View 13232 LONGACRE DRIVE Windermere, FL MLS# O6372809
$650,000
5

Beds

3.0

Baths

2,511

Sq.Ft.

13232 LONGACRE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6956 TRELLIS VINE LOOP Windermere, FL MLS# O6401639
$650,000
5

Beds

4.0

Baths

3,015

Sq.Ft.

6956 TRELLIS VINE LOOP

Windermere, FL

Courtesy of EAST PEARL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 12633 HADDON DRIVE Windermere, FL MLS# O6411199
$650,000
5

Beds

3.1

Baths

3,000

Sq.Ft.

12633 HADDON DRIVE

Windermere, FL

View 9110 PALM TREE DRIVE Windermere, FL MLS# O6414631
$650,000
3

Beds

2.0

Baths

1,819

Sq.Ft.

9110 PALM TREE DRIVE

Windermere, FL

View 12912 DROXFORD ROAD Windermere, FL MLS# O6422064
  • Recently Listed with Virtual Tour
1 of 52
$650,000
5

Beds

3.1

Baths

2,966

Sq.Ft.

12912 DROXFORD ROAD

Windermere, FL

View 811 MAIN STREET Windermere, FL MLS# O6409463
  • Virtual Tour
1 of 33
$649,999
2

Beds

1.1

Baths

1,398

Sq.Ft.

811 MAIN STREET

Windermere, FL

Courtesy of CAMERON REALTY GROUP LLC
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 13013 OVERSTREET ROAD Windermere, FL MLS# O6380917
$639,994
4

Beds

2.1

Baths

2,053

Sq.Ft.

13013 OVERSTREET ROAD

Windermere, FL

View 6558 HELMSLEY CIRCLE Windermere, FL MLS# S5151342
  • Virtual Tour
1 of 55
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 13622 DARCHANCE ROAD Windermere, FL MLS# S5146266
$629,900
3

Beds

2.0

Baths

2,147

Sq.Ft.

13622 DARCHANCE ROAD

Windermere, FL

View 6601 DUNCASTER STREET Windermere, FL MLS# O6416272
$627,900
4

Beds

3.0

Baths

3,001

Sq.Ft.

6601 DUNCASTER STREET

Windermere, FL

View 8632 ABBOTSBURY DRIVE Windermere, FL MLS# O6406433
$625,000
4

Beds

3.1

Baths

2,720

Sq.Ft.

8632 ABBOTSBURY DRIVE

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 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

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 6644 SAWYER SHORES LANE Windermere, FL MLS# O6417657
$600,000
Studio

Beds

0.0

Baths

6644 SAWYER SHORES LANE

Windermere, FL

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 1516 HEMPEL AVENUE Windermere, FL MLS# O6342593
$595,000
Studio

Beds

0.0

Baths

1516 HEMPEL 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

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

356

Estimated median home price

$1,098,500
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 - 500K35
$500K - 600K32
$600K - 700K28
$700K - 800K20
$800K - 900K19
$900K - 1M14
$1M - Max185

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family282
Townhouse47
Condo9
Commercial1
Rental84
Lots and Land17
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/4/2026)

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 7/4/2026.