220 North Road

Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation buffer runs along the length of the back of the property for further privacy. Just across North Road from the ancient way is the walking entrance to Great Rock Bight. If you enjoy the splendid rural nature of upisland Chilmark, then this is your place. MAIN HOUSE: The rich wooden interior radiates warmth and relaxation and is enhanced by the living room's floor-to-cathedral-ceiling natural stone fireplace. A large deck wraps around nearly half the house, giving you treehouse-like views and a magical setting for outdoor entertaining. GUEST COTTAGE: This intimate log-home is a separate getaway, hidden by a clutch of tall trees nearly 100 yards away from the main house which creates highly protected privacy. Flowers and herb gardens surround its sunny deck, creating a peaceful nook for reading and relaxation. A detached bedroom is like a honeymoon retreat that summer guests will love. A new, 3BR septic system was just installed (July 2026). EACH HOUSE HAS its own septic system and well, making them truly separate and independent. There's room for a swimming pool near the Main House. Leave the congestion of down-island comfortably behind, while enjoying easy recreation access to public lands and beaches (Lucy Vincent, Squibnocket), sailing on Quitsa & Menemsha ponds, and proximity to Menemsha and the Chilmark Store, community center and famed Chilmark Tavern. ASK ABOUT partial Seller financing. Also, ASK ABOUT about Seller lease-back of the Guest Cottage which could significantly reduce the purchase price. Note: Lease-back is an option, not a contingency for a sale to happen.