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 2:57 PM
| Class | Total | Price | Beds | Baths | Age |
|---|---|---|---|---|---|
| Residential | 17 | $5,519,823 | 4.6 | 4.6 | 29.4 |
9725 Chestnut Ridge Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6370294 / Active
Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.Spannin...
Reduced -$150,000
5074 Isleworth Country Club Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6373191 / Active
A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of ...
Reduced -$345,000
5001 Latrobe Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6389183 / Active
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...
Reduced -$200,000
9832 Laurel Valley Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6416194 / Active
Virtually Staged. https://iframe.videodelivery.net/7c8847db18d8a7617d27c5577c88508f A true Lake Butler trophy estate. Set within the world-famous g...
5151 Latrobe Dr
Windermere, FL 34786
Isleworth
Residential
MLS# O6392380 / Active
Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms ...
Reduced -$200,000
5138 Fairway Oaks Dr
Windermere, FL 34786
Isleworth
Residential
MLS# O6401757 / Active
Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Is...
5050 Isleworth Country Club Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6372348 / Active
Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout ...
Reduced -$285,000
9144 Isleworth Gardens Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6397842 / Active
Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This imp...
4819 Alexandra Garden Court
Windermere, FL 34786
Isleworth
Residential
MLS# O6330108 / Active
Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this be...
9731 Chestnut Ridge Drive
Windermere, FL 34786
Isleworth
Residential
MLS# O6336655 / Active
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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MLS IDX data last updated on 06-17-2026 2:04 PM EST.