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 2:45 PM

Class Total Price Beds Baths Age
Residential 17 $5,519,823 4.6 4.6 29.4
Displaying results 1-10 of 17
70 Photos 9832 Laurel Valley Drive Windermere, FL 34786

9832 Laurel Valley Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6416194 / Active
6 Beds, 10.00 Total Baths, 7 Full Bath, 3 Half Bath, 11100 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Virtually Staged. https://iframe.videodelivery.net/7c8847db18d8a7617d27c5577c88508f A true Lake Butler trophy estate. Set within the world-famous g... 

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$13,900,000
Provided courtesy of REAL BROKER, LLC
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 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
46 Photos 6462 Deacon Cir Windermere, FL 34786

6462 Deacon Cir
Windermere, FL 34786
Isleworth
Residential

MLS# O6407107 / Active
5 Beds, 6.00 Total Baths, 4 Full Bath, 2 Half Bath, 7178 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary wat... 

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$6,950,000
Provided courtesy of ISLEWORTH REALTY LLC
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
51 Photos 5138 Fairway Oaks Dr Windermere, FL 34786

5138 Fairway Oaks Dr
Windermere, FL 34786
Isleworth
Residential

MLS# O6401757 / Active
4 Beds, 5.00 Total Baths, 5 Full Bath, 4330 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Is... 

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$5,500,000
Provided courtesy of ISLEWORTH REALTY LLC
64 Photos 5199 Latrobe Dr Windermere, FL 34786

5199 Latrobe Dr
Windermere, FL 34786
Isleworth
Residential

MLS# O6409961 / Active
6 Beds, 7.00 Total Baths, 6 Full Bath, 1 Half Bath, 4665 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined... 

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$5,300,000
Provided courtesy of ISLEWORTH REALTY LLC
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
63 Photos 9144 Isleworth Gardens Drive Windermere, FL 34786

9144 Isleworth Gardens Drive
Windermere, FL 34786
Isleworth
Residential

MLS# O6397842 / Active
3 Beds, 5.00 Total Baths, 3 Full Bath, 2 Half Bath, 5004 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This imp... 

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$4,450,000
Provided courtesy of MEGAN DOWDY REALTY, LLC
57 Photos 5151 Latrobe Dr Windermere, FL 34786

5151 Latrobe Dr
Windermere, FL 34786
Isleworth
Residential

MLS# O6392380 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 5301 Sqft
Area: 34786 - Windermere, Subdivision: Isleworth

Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms ... 

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$3,900,000
Reduced -$200,000
Provided courtesy of ISLEWORTH REALTY LLC

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