Market Snapshot of Listings in isleworth - Windermere, FL 34786
The current prices for all Real Estate Listings in isleworth - Windermere, FL are reflected in the the table below.

Market Snapshot

Averages based on current search criteria as of 06/17/2026 1:21 PM

Class Total Price Beds Baths Age
Residential 17 $5,519,823 4.6 4.6 29.4
Displaying results 1-10 of 17
44 Photos 4819 Alexandra Garden Court Windermere, FL 34786

4819 Alexandra Garden Court
Windermere, FL 34786
Isleworth
Residential

MLS# O6330108 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 3745 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this be... 

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$3,200,000
Provided courtesy of ISLEWORTH REALTY LLC
57 Photos 9731 Chestnut Ridge Drive Windermere, FL 34786

9731 Chestnut Ridge Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6336655 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 4877 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and show... 

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$3,400,000
Provided courtesy of ISLEWORTH REALTY LLC
66 Photos 4812 Alexandra Garden Court Windermere, FL 34786

4812 Alexandra Garden Court
Windermere, FL 34786
Isleworth
Residential

MLS# O6339134 / Active
3 Beds, 5.00 Total Baths, 3 Full Bath, 2 Half Bath, 4262 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residen... 

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$3,699,000
Provided courtesy of STOCKWORTH REALTY GROUP
65 Photos 5243 Isleworth Country Club Drive Windermere, FL 34786

5243 Isleworth Country Club Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6348067 / Active
4 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 6424 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely... 

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$5,100,000
Reduced -$225,000
Provided courtesy of STOCKWORTH REALTY GROUP
61 Photos 9725 Chestnut Ridge Drive Windermere, FL 34786

9725 Chestnut Ridge Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6370294 / Active
7 Beds, 7.00 Total Baths, 5 Full Bath, 2 Half Bath, 8000 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.Spannin... 

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$6,000,000
Reduced -$150,000
Provided courtesy of DOUGLAS ELLIMAN
40 Photos 5050 Isleworth Country Club Drive Windermere, FL 34786

5050 Isleworth Country Club Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6372348 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 3365 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout ... 

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$3,690,000
Reduced -$285,000
Provided courtesy of COMPASS FLORIDA LLC
70 Photos 5074 Isleworth Country Club Drive Windermere, FL 34786

5074 Isleworth Country Club Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6373191 / Active
5 Beds, 7.00 Total Baths, 6 Full Bath, 1 Half Bath, 7099 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of ... 

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$7,250,000
Reduced -$345,000
Provided courtesy of MEM REALTY GROUP
70 Photos 9323 Gladys Garden Court Windermere, FL 34786

9323 Gladys Garden Court
Windermere, FL 34786
Isleworth
Residential

MLS# O6381880 / Active
6 Beds, 10.00 Total Baths, 6 Full Bath, 4 Half Bath, 9770 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a maste... 

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$11,900,000
Reduced -$600,000
Provided courtesy of CORCORAN PREMIER REALTY
70 Photos 5145 Latrobe Drive Windermere, FL 34786

5145 Latrobe Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6382287 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 4512 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar a... 

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$3,299,000
Reduced -$150,000
Provided courtesy of SOUTHERN REALTY GROUP LLC
40 Photos 5001 Latrobe Drive Windermere, FL 34786

5001 Latrobe Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6389183 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 4417 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Cou... 

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$3,299,999
Reduced -$200,000
Provided courtesy of Q BOUTIQUE SPECIALTY REALTY INC

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