View 9731 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6336655
$3,400,000
4

Beds

4.0

Baths

4,877

Sq.Ft.

9731 CHESTNUT RIDGE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6372348
$3,390,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 5001 LATROBE DRIVE Windermere, FL MLS# O6389183
$3,299,999
5

Beds

4.1

Baths

4,417

Sq.Ft.

5001 LATROBE DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 5145 LATROBE DRIVE Windermere, FL MLS# O6382287
$3,299,000
4

Beds

4.1

Baths

4,512

Sq.Ft.

5145 LATROBE DRIVE

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 4819 ALEXANDRA GARDEN COURT Windermere, FL MLS# O6330108
$3,200,000
4

Beds

4.1

Baths

3,745

Sq.Ft.

4819 ALEXANDRA GARDEN COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 2 CHASE ROAD Windermere, FL MLS# O6345197
  • New Construction
1 of 3
$3,200,000
4

Beds

4.1

Baths

3,889

Sq.Ft.

2 CHASE ROAD

Windermere, FL

Courtesy of REAL BROKER, LLC
View 5073 LATROBE DR Windermere, FL MLS# O6414325
  • Recently Listed
1 of 34
$2,999,000
4

Beds

4.2

Baths

4,706

Sq.Ft.

5073 LATROBE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 9226 BAYWAY DRIVE Orlando, FL MLS# O6405499
$2,850,000
6

Beds

5.1

Baths

5,528

Sq.Ft.

9226 BAYWAY DRIVE

Orlando, FL

Courtesy of CINO INTERNATIONAL INC
View 606 E 6TH AVENUE Windermere, FL MLS# O6390327
  • Virtual Tour
1 of 42
$2,350,000
4

Beds

4.1

Baths

4,471

Sq.Ft.

606 E 6TH AVENUE

Windermere, FL

Courtesy of ELITE GLOBAL REAL ESTATE LLC
View 6550 CARTMEL LANE Windermere, FL MLS# O6396111
  • Virtual Tour
1 of 32
$2,190,000
4

Beds

4.1

Baths

4,257

Sq.Ft.

6550 CARTMEL LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11051 HAWKSHEAD COURT Windermere, FL MLS# O6400963
$1,895,000
5

Beds

4.2

Baths

3,728

Sq.Ft.

11051 HAWKSHEAD COURT

Windermere, FL

Courtesy of REAL BROKER, LLC
View 5719 EMERSON POINTE WAY Orlando, FL MLS# O6397588
$1,799,500
6

Beds

5.1

Baths

5,722

Sq.Ft.

5719 EMERSON POINTE WAY

Orlando, FL

Courtesy of PREMIER PROPERTIES LLC
View 5727 EMERINGTON CRESCENT Orlando, FL MLS# O6335398
$1,799,000
Studio

Beds

0.0

Baths

5727 EMERINGTON CRESCENT

Orlando, FL

Courtesy of PROPERTY INVESTMENT BROKERS
View 5626 BAY SIDE DRIVE Orlando, FL MLS# O6408896
  • Virtual Tour
1 of 50
$1,745,000
4

Beds

3.2

Baths

3,433

Sq.Ft.

5626 BAY SIDE DRIVE

Orlando, FL

Courtesy of COLDWELL BANKER REALTY
View 5509 EMERSON POINTE WAY Orlando, FL MLS# O6369643
$1,690,000
6

Beds

5.0

Baths

4,296

Sq.Ft.

5509 EMERSON POINTE WAY

Orlando, FL

Courtesy of CROWN REALTY INT-L LLC
View 11015 HAWKSHEAD COURT Windermere, FL MLS# O6405977
$1,499,999
5

Beds

4.1

Baths

3,868

Sq.Ft.

11015 HAWKSHEAD COURT

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 109 E 12TH AVENUE Windermere, FL MLS# O6394569
  • Virtual Tour
1 of 43
$1,198,000
4

Beds

3.1

Baths

2,791

Sq.Ft.

109 E 12TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 11162 LEDGEMENT LANE Windermere, FL MLS# O6346461
$995,000
4

Beds

3.1

Baths

3,248

Sq.Ft.

11162 LEDGEMENT LANE

Windermere, FL

Courtesy of INFINITY REALTY GROUP LLC
View 1002 OAKDALE STREET Windermere, FL MLS# TB8495717
$975,000
4

Beds

3.0

Baths

3,516

Sq.Ft.

1002 OAKDALE STREET

Windermere, FL

Courtesy of KELLER WILLIAMS SUBURBAN TAMPA
View 9113 IVEY HILL COURT Orlando, FL MLS# S5151134
  • Recently Listed with Virtual Tour
1 of 55
$975,000
5

Beds

3.0

Baths

2,872

Sq.Ft.

9113 IVEY HILL COURT

Orlando, FL

Courtesy of WATSON REALTY CORP

About Isleworth

Listings in Isleworth, Windermere, FL

55

Estimated median home price

$2,850,000
Isleworth, Windermere Real Estate

Search Isleworth, Florida Real Estate Listings & New Homes for Sale in Isleworth, FL. Find Isleworth Houses, Townhouses, Condos, & Properties for Sale at Weichert.com

Homes for Sale by Price in Isleworth, Windermere, FL

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K0
$400K - 500K0
$500K - 600K4
$600K - 700K4
$700K - 800K2
$800K - 900K2
$900K - 1M6
$1M - Max37

Homes for Sale by Type in Isleworth, Windermere, FL

Property TypeCount
Single Family51
Townhouse0
Condo0
Commercial0
Rental7
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/16/2026)

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 6/16/2026.