A RARE CHAPPAQUIDDICK LEGACY ESTATE -- Privacy & Island Living at its finest. Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-acre multi-residence estate, with 4 conforming parcels, on Martha's Vineyard's treasured Chappaquiddick Island is more than a property--it's a rare opportunity to create a generational legacy in one of New England's most sought-after coastal enclaves. Tucked beside the historic Royal & Ancient Chappaquiddick Links and surrounded by conservation land, this compound offers unmatched seclusion while placing you moments from sandy beaches, island trails, and the gentle rhythm of Vineyard life. Main Residence | 8,335 sq. ft. Chef's kitchen with Viking oven, dual Sub-Zero refrigerators, wine fridge, and granite counters. Expansive decks for morning coffee at sunrise and cocktail hours at sunset. Lower level with wet bar opening to pool and patio; private home office for remote work in paradise. Second Residence | 1,351 sq. ft. - 3 bedrooms, 2 bathrooms, full kitchen, screened-in porch, multi-level deck, and outdoor shower. Bunk House Retreat | 1 bedroom, kitchenette, living area, and full bath  perfect for overflow guests or a quiet getaway. Resort-Style Amenities include a Heated Gunite pool with outdoor shower, a Tennis court for friendly matches and a 4-bay garage with room for all the toys. Multiple parcels offering flexibility for expansion, this property invites you to imagine a lifetime of gatherings, celebrations, and quiet escapes. Opportunities of this scale and privacy on Chappaquiddick are exceedingly rareand once gone, they may never come again. Ready for its next chapter, this property awaits a discerning new steward to restore its former glory and carry it proudly into the future. Call now to arrange a private tour and experience firsthand what it means to live surrounded by natural beauty, boundless privacy, and the authentic Chappy way of life. NOTE: The images and photographs provided are for illustrative purposes only and may not reflect the current state if the state, features, or furnishings of the property. Prospective buyers are encouraged to conduct their own inspections and due diligence to verify all details prior to making any purchase decisions.