View 5525 ISLEWORTH COUNTRY CLUB DR Windermere, FL MLS# O6304800
$14,250,000
5

Beds

5.1

Baths

9,511

Sq.Ft.

5525 ISLEWORTH COUNTRY CLUB DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 9323 GLADYS GARDEN COURT Windermere, FL MLS# O6381880
  • Recently Listed with Virtual Tour
1 of 84
$13,995,000
6

Beds

6.4

Baths

9,770

Sq.Ft.

9323 GLADYS GARDEN COURT

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 5074 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6373191
$7,595,000
5

Beds

6.1

Baths

6,937

Sq.Ft.

5074 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of MEMARPOURI REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9725 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6370294
$6,950,000
7

Beds

5.2

Baths

8,000

Sq.Ft.

9725 CHESTNUT RIDGE DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 5186 VARDON DRIVE Windermere, FL MLS# O6382040
  • Recently Listed with Virtual Tour
1 of 61
$5,680,000
6

Beds

6.0

Baths

5,376

Sq.Ft.

5186 VARDON DRIVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 6117 LOUISE COVE DRIVE Windermere, FL MLS# O6372197
$5,400,000
4

Beds

4.1

Baths

5,752

Sq.Ft.

6117 LOUISE COVE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5243 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6348067
$5,325,000
4

Beds

5.1

Baths

6,424

Sq.Ft.

5243 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5036 LATROBE DRIVE Windermere, FL MLS# O6346003
$4,900,000
5

Beds

4.1

Baths

5,548

Sq.Ft.

5036 LATROBE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5745 EMERINGTON CRESCENT Orlando, FL MLS# O6382015
  • Recently Listed with Virtual Tour
1 of 100
$4,590,000
7

Beds

7.1

Baths

7,881

Sq.Ft.

5745 EMERINGTON CRESCENT

Orlando, FL

Courtesy of EXP REALTY LLC
View 5727 EMERINGTON CRESCENT Orlando, FL MLS# O6380297
  • Recently Listed with Virtual Tour
1 of 9
$4,500,000
5

Beds

5.1

Baths

7,621

Sq.Ft.

5727 EMERINGTON CRESCENT

Orlando, FL

Courtesy of PROPERTY INVESTMENT BROKERS
View 9648 MCCORMICK PLACE Windermere, FL MLS# O6346918
$3,800,000
3

Beds

3.1

Baths

4,751

Sq.Ft.

9648 MCCORMICK PLACE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 4812 ALEXANDRA GARDEN COURT Windermere, FL MLS# O6339134
$3,699,000
3

Beds

3.2

Baths

4,262

Sq.Ft.

4812 ALEXANDRA GARDEN COURT

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6372348
$3,690,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 5145 LATROBE DRIVE Windermere, FL MLS# O6382287
  • Recently Listed with Virtual Tour
1 of 73
$3,499,000
4

Beds

4.1

Baths

4,512

Sq.Ft.

5145 LATROBE DRIVE

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
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 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 5410 BAY SIDE DRIVE Orlando, FL MLS# O6324381
  • Virtual Tour
1 of 52
$2,950,000
4

Beds

4.0

Baths

3,479

Sq.Ft.

5410 BAY SIDE DRIVE

Orlando, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 6248 LOUISE COVE DR Windermere, FL MLS# O6378223
  • Recently Listed
1 of 71
$2,850,000
5

Beds

5.1

Baths

6,253

Sq.Ft.

6248 LOUISE COVE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 9111 MID PINES COURT Orlando, FL MLS# O6377235
  • Virtual Tour
1 of 67
$2,400,000
5

Beds

4.1

Baths

5,315

Sq.Ft.

9111 MID PINES COURT

Orlando, FL

Courtesy of THE AGENCY FL

About Isleworth

Listings in Isleworth, Windermere, FL

47

Estimated median home price

$1,790,000
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 - 500K1
$500K - 600K1
$600K - 700K5
$700K - 800K2
$800K - 900K4
$900K - 1M3
$1M - Max31

Homes for Sale by Type in Isleworth, Windermere, FL

Property TypeCount
Single Family43
Townhouse0
Condo0
Commercial0
Rental5
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/21/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 2/22/2026.

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 2/22/2026.