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 9826 LAUREL VALLEY DRIVE Windermere, FL MLS# O6345711
$5,900,000
5

Beds

4.2

Baths

7,491

Sq.Ft.

9826 LAUREL VALLEY DRIVE

Windermere, FL

Courtesy of EXP REALTY LLC
View 5550 OSPREY ISLE LANE Orlando, FL MLS# O6303377
$5,695,000
5

Beds

5.1

Baths

6,730

Sq.Ft.

5550 OSPREY ISLE LANE

Orlando, FL

Courtesy of SOUTHERN REALTY GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 5199 LATROBE DRIVE Windermere, FL MLS# O6315618
$5,494,000
5

Beds

6.1

Baths

4,665

Sq.Ft.

5199 LATROBE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
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 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 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 4711 JOANNA GARDEN CT Windermere, FL MLS# O6359789
$3,250,000
3

Beds

3.1

Baths

4,089

Sq.Ft.

4711 JOANNA GARDEN CT

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
$3,150,000
4

Beds

4.0

Baths

3,479

Sq.Ft.

5410 BAY SIDE DRIVE

Orlando, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 6120 PAYNE STEWART DR Windermere, FL MLS# O6288273
$2,700,000
4

Beds

4.1

Baths

3,636

Sq.Ft.

6120 PAYNE STEWART DR

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 11019 ULLSWATER LANE Windermere, FL MLS# O6350027
$2,495,000
5

Beds

4.1

Baths

5,916

Sq.Ft.

11019 ULLSWATER LANE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 1020 OAKDALE STREET Windermere, FL MLS# O6322270
  • New Construction with Virtual Tour
1 of 13
$2,200,000
5

Beds

4.1

Baths

3,994

Sq.Ft.

1020 OAKDALE STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 5750 EMERINGTON CRES Orlando, FL MLS# O6356206
  • Virtual Tour
1 of 97
$2,190,000
5

Beds

6.0

Baths

5,838

Sq.Ft.

5750 EMERINGTON CRES

Orlando, FL

Courtesy of THE SIMON SIMAAN GROUP
View 5727 EMERINGTON CRESCENT Orlando, FL MLS# O6335398
$1,995,000
Studio

Beds

0.0

Baths

5727 EMERINGTON CRESCENT

Orlando, FL

Courtesy of PROPERTY INVESTMENT BROKERS
View 11015 HAWKSHEAD COURT Windermere, FL MLS# O6316990
$1,700,000
5

Beds

4.1

Baths

3,868

Sq.Ft.

11015 HAWKSHEAD COURT

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 11019 KENTMERE COURT Windermere, FL MLS# O6303131
$1,500,000
4

Beds

4.0

Baths

3,813

Sq.Ft.

11019 KENTMERE COURT

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 6443 CARTMEL LANE Windermere, FL MLS# O6179128
  • Virtual Tour
1 of 31
$1,475,000
5

Beds

4.1

Baths

4,257

Sq.Ft.

6443 CARTMEL LANE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP

About Isleworth

Listings in Isleworth, Windermere, FL

43

Estimated median home price

$1,299,000
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 - 600K1
$600K - 700K4
$700K - 800K4
$800K - 900K4
$900K - 1M5
$1M - Max25

Homes for Sale by Type in Isleworth, Windermere, FL

Property TypeCount
Single Family40
Townhouse0
Condo0
Commercial0
Rental5
Lots and Land3
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/17/2025)

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 12/18/2025.

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 12/18/2025.