Welcome to 58 Wainscott Stone Road, a timeless Hamptons classic situated on a 5.4-acre property in Wainscott South. The 13,400 +/- square foot gated estate is surrounded by a 10-acre reserve with a natural pond, enhancing the home's bucolic setting. This home offers unparalleled privacy just minutes from the storied Georgica Pond and pristine Atlantic ocean beaches. As you enter the home, you're welcomed by the light-filled grand foyer with its double height ceilings. The main level features a living room with a wood-burning fireplace directly off the kitchen, an elegant dining room, library, formal living room and sunroom each with its own gas lit fireplaces. The chef's kitchen, designed by Christopher Peacock, is equipped with top-of-the-line appliances, a butler's pantry, and a wet bar, ideal for culinary enthusiasts. This level is complete with a junior primary suite, a versatile room with full bathroom perfect for a home office, laundry and mud room. 58 Wainscott Stone is designed for both effortless entertaining and everyday comfort in mind which seamlessly opens to an expansive bluestone patio, with a fully equipped outdoor kitchen. Upstairs, the primary suite serves as a serene retreat with the sitting room and bedroom opening up to two separate terraces, dual walk-in closets, and a spa-like en suite bath including a double-sink vanity and soaking tub. Six additional en suite bedrooms provide ample space for family and guests. A convenient laundry room and elevator servicing all three levels complete the second floor. The finished lower level features a walk-in wine cellar, gym with steam shower and sauna, a screening room, and spacious recreation areas complete with a half bath. Two additional rooms and a full bath on the lower level offers more flexible space. The meticulously landscaped grounds with expansive lawns are ideal for both relaxation and entertainment, creating an unparalleled outdoor living experience. Bluestone patios surround a 60' x 20' heated gunite pool with spa perfect for lounging, dining, and soaking in the beautiful surroundings. The 545 +/- square foot craftsman studio adds another level to this unique property with its inviting lounge area, full bath, laundry, kitchenette, and outdoor shower. A sunken hard court tennis, half basketball court, custom treehouse, and attached 3-car garage complete this offering. Positioned south of the highway, this estate provides access to beloved farm stands and the coveted Beach Lane and Town Line Beach. Experience luxury living at this Wainscott South retreat, where every detail has been thoughtfully crafted.