Welcome to 300 Hill Street, an impeccably restored historic residence in the heart of Southampton Village, where classic charm meets modern luxury. Ideally situated south of the highway, this distinguished shingle-style estate spans approximately 5,000+ square feet on a beautifully landscaped 0.43-acre gated property - a rare offering in one of The Hamptons' most coveted neighborhoods. Originally built in the late 19th century and thoughtfully renovated, this exceptional compound seamlessly blends period character with today's lifestyle amenities. The main residence features four bedrooms, soaring ceilings, with light-filled rooms that enhance a sense of warmth and sophistication throughout. Thoughtful architectural details and generous living spaces include formal living and dining rooms, cozy sunlit conservatory and sunroom spaces, and an airy, eat-in chef's kitchen (two dishwashers) - ideal for both relaxed family living and sophisticated entertaining. Transition outdoors to discover your private oasis: a heated gunite pool with adjacent cabana, lush garden settings, and outdoor spaces that extend the home's living areas seamlessly into nature. A separate guest house adds versatility and privacy, boasting additional bedrooms (one bedroom with gym or two bedrooms), baths, a living area with fireplace, and its own kitchenette. Outdoor fireplace, grill, and pizza oven, private community tennis court around the corner. This iconic Southampton address offers unmatched convenience: in close proximity to boutique shops, acclaimed restaurants, cultural attractions, and the vibrant energy of Southampton's village core. Nearby pristine beaches and recreational amenities make this an attractive retreat for summer. 300 Hill Street - where historic elegance, modern comfort, and premier village living come together.