An Ultra Rare Generational compound opportunity awaits in the heart of the Amagansett Lanes with this exceptional offering, combining two masterfully designed luxury homes on an acre of meticulously landscaped grounds. Combined, the properties offer over 13,000± sq. ft., 11 bedrooms, 10 full and 4 Half baths, and an extraordinary array of indoor and outdoor amenities, creating a private coastal estate unlike any other. 109 Hand Lane, developed by the owners of Manhattan's iconic The Lowell, spans over 10,000± sq. ft. across .66± acres, featuring Venetian plaster walls, reclaimed beam ceilings, Chesney limestone fireplaces, and a chef's kitchen with Sub-Zero, Miele, and Wolf appliances. Entertaining flows effortlessly to the outdoors, with a 20x45 heated Gunite pool, two-story pool house/cabana, Mahogany shower, multiple terraces, and dual firepit experiences. The lower level extends the home's luxurious atmosphere with soaring ceilings, a billiard room with wet bar, a striking wine room, and three additional en-suite bedrooms. 103 Hand Lane, designed by award-winning interior designer Amalia Graziani, spans 3,300± sq. ft. on .37 +/- acres bordering a reserve. The home blends understated sophistication with warmth, offering 4 bedrooms, 4.5 baths, a chef's kitchen with marble countertops, wood-paneled living spaces with stone fireplaces, and a first-floor primary suite with vaulted ceilings and spa-inspired bath. Outdoors, a heated Gunite pool, backyard firepit, state-of-the-art grill, and expansive terraces provide an ideal setting for both relaxation and entertaining, all just moments from the ocean, farm stands, and acclaimed restaurants. This rare compound offers unmatched scale, privacy, and versatility, perfect for multi-generational living, grand-scale entertaining, or an expansive private retreat. Properties combining this size, design, and setting are exceptionally rare making this a singular opportunity to own a true Hamptons legacy, a private enclave that seamlessly marries timeless elegance, modern comfort, and the quintessential luxurious lifestyle.