Isleworth One of the most prestigious private golf club communities Featured Listings in Isleworth New Listing - 6 days on site1 / 51$5,500,0004BEDS5TOTAL BATHS4,330SQFT5138 FAIRWAY OAKS DR WINDERMERE, FL 34786Single Family Residence For Sale- ActiveSet along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompa1 / 57$4,100,0004BEDS5TOTAL BATHS5,301SQFT5151 LATROBE DR WINDERMERE, FL 34786Single Family Residence For Sale- ActivePositioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence re1 / 78$3,499,9995BEDS5TOTAL BATHS4,417SQFT5001 LATROBE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveOne or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own a stunning estate home in the prestigious Isleworth Golf & Country Club, perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lak1 / 45$4,950,0003BEDS4TOTAL BATHS2,983SQFT6113 PAYNE STEWART DRIVE WINDERMERE, FL 34786Townhouse For Sale- PendingUnder contract-accepting backup offers. Timeless Waterfront Elegance in Isleworth’s Golf Villas Perfectly positioned along the tranquil shoreline of Lake Chase — part of the coveted Butler Chain of Lakes — this exquisitely renovated residence ofPrice Change - 3 weeks ago1 / 73$3,449,0004BEDS5TOTAL BATHS4,512SQFT5145 LATROBE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveWelcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for Price Change - a week ago1 / 61$6,980,0004BEDS5TOTAL BATHS4,739SQFT5186 VARDON DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveOne or more photo(s) has been virtually staged. Fully reimagined golf-front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre, this 4,739 sq ft residence offers 4 bedrooms and 4Price Change - 4 weeks ago1 / 84$12,500,0006BEDS10TOTAL BATHS9,770SQFT9323 GLADYS GARDEN COURT WINDERMERE, FL 34786Single Family Residence For Sale- ActiveBrand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled roo1 / 81$7,595,0005BEDS7TOTAL BATHS6,937SQFT5074 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveA masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 6,900 square feet of refined l1 / 40$3,390,0004BEDS5TOTAL BATHS3,365SQFT5050 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveSituated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, frPrice Change - 2 weeks ago1 / 57$6,150,0007BEDS7TOTAL BATHS8,000SQFT9725 CHESTNUT RIDGE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveNewly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood de1 / 65$5,100,0004BEDS6TOTAL BATHS6,424SQFT5243 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActivePresenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, t1 / 47$4,900,0005BEDS5TOTAL BATHS5,548SQFT5036 LATROBE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square1 / 61$3,800,0003BEDS4TOTAL BATHS4,751SQFT9648 MCCORMICK PLACE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveStunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square f1 / 66$3,699,0003BEDS5TOTAL BATHS4,262SQFT4812 ALEXANDRA GARDEN COURT WINDERMERE, FL 34786Single Family Residence For Sale- ActiveLuxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the 1 / 57$3,400,0004BEDS4TOTAL BATHS4,877SQFT9731 CHESTNUT RIDGE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveNestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dinin1 / 44$3,200,0004BEDS5TOTAL BATHS3,745SQFT4819 ALEXANDRA GARDEN COURT WINDERMERE, FL 34786Single Family Residence For Sale- ActiveDiscover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to 1 / 100$14,250,0005BEDS6TOTAL BATHS9,511SQFT5525 ISLEWORTH COUNTRY CLUB DR WINDERMERE, FL 34786Single Family Residence For Sale- PendingUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in thSee All Results