Isleworth One of the most prestigious private golf club communities Featured Listings in Isleworth New Listing - 2 weeks on site1 / 83$7,595,0005BEDS7TOTAL BATHS6,937SQFT5074 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActiveLuxury living perfectly positioned along the 6th fairway in the world-renowned guard-gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space which includes over 2,400 square foot addition upsNew Listing - 3 weeks on site1 / 40$3,690,0004BEDS5TOTAL 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, frNew Listing - 4 weeks on site1 / 57$6,950,0007BEDS7TOTAL BATHS8,000SQFT9725 CHESTNUT RIDGE DRIVE WINDERMERE, FL 34786Single Family Residence For Sale- ActivePrivate showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approxim1 / 67$3,250,0003BEDS4TOTAL BATHS4,089SQFT4711 JOANNA GARDEN CT WINDERMERE, FL 34786Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally desig1 / 65$5,325,0004BEDS6TOTAL 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- ActiveWithin 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 square-foot residence unfolds across two level1 / 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 residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear o1 / 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- ActiveOne 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 the world. Designed by architect Terry IrwSee All Results