Located in the heart of the prestigious Southampton Estate Section, this timeless 1891 residence is being offered for the first time since 1990. Just moments from the Village and pristine beaches, the estate blends historic character with graceful living across 1.23 acres of lush, private grounds, featuring a pool, tennis court, and a legal guest house. Thoughtfully updated while preserving its original charm, the home features high ceilings, oversized windows, and abundant natural light that fills every room. Iconic Dutch doors, wide-plank wood floors, and antique details speak to the home's storied past, while nearly every room opens to inviting outdoor living spaces, perfect for entertaining or quiet retreats. The main residence offers 6 bedrooms, 5 full bathrooms, and a powder room, including a poolside cabana bath. The sunlit kitchen flows seamlessly to a spacious deck, ideal for summer gatherings, while the private pool and surrounding lush gardens offer serene seclusion. A standout feature is the rare, grandfathered-in terrace off the primary suite-a coveted outdoor escape that adds both charm and value. Completing the estate is a legal guest house, full of original barn-style character, offering 1 bedrooms, 2 bathrooms, a living room, and authentic details such as wide-plank wood floors and antique windows. With private tennis, mature landscaping, and unmatched historical appeal, this extraordinary property is a once-in-a-generation opportunity in one of the most sought-after locations in the Hamptons. A timeless Southampton classic-rich in history, grandfathered-in amenities, natural light, and lifestyle.