Discover the quintessential Sag Harbor lifestyle in this spacious and meticulously maintained home, ideally situated in the coveted Historic District. Just a short distance from Main Street and Haven's Beach, 20 Hamilton Street offers the perfect blend of classic charm and modern convenience. The open floor plan, perfect for entertainment, seamlessly connects the living room, dining room, and the eat-in kitchen, featuring top-of-the-line appliances like a Jenn-Air six-burner gas stove, Sub-Zero fridge, U-Line wine fridge, Avalon bottleless water cooler, and a Bosch dishwasher. This classic home boasts four bedrooms, including a generously sized en suite primary bedroom on the first floor. In addition there's a versatile office/den and a welcoming media/family room, providing different ambiances for everyone. Three full baths complete the indoor layout. Outside, the beautifully landscaped backyard with a spacious patio deck overlooking the heated pool (34x14) offers your own private oasis. In addition, the attached one-car garage with an electric car charger provides modern convenience. With its classic charm and serene location on a quiet street, this Sag Harbor treasure offers a lifestyle that's both timeless and convenient.