220 North Road, Chilmark

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.

First Floor

The first floor is entered via the large deck which leads to an atrium-like dining room and kitchen. The living room features a floor-to-ceiling natural stone fireplace with insert. Hanging dramatically from the rafters of the cathedral ceiling is a wooden rowing shell which reflects the abundant light streaming in through a pair of 8-foot sliders which open out to an expansive deck, ideal for dinner parties and entertaining. The primary bedroom suite and second bedroom with bath are also on this floor.

Second Floor

A loft area above the kitchen features the 3rd bedroom.

Basement

The lower level is partially finished with a living room, bedroom and full bath. There is also significant storage space for sailfish/sunfish and other equipment. Washer/dryer is located on this level.

Parking

On-site

Other Buildings

Boat Shed w/ Main House; Shed w/ Guest Cottage

Second Dwelling

The Guest Cottage (1990) is a log home with honeyed interior walls that create an ideal honeymoon or getaway retreat. There are two bedrooms, plus a third, detached bedroom that is set apart by overhanging trees in a truly magical setting. The living/dining room is warmed by a stone fireplace with a wood stove insert. Herb gardens and flowers embrace the outside, creating a quiet and inviting space. There is an outdoor shower and hot tub. The cottage has it own well and its own newly installed 3BR septic system.