345 North Road, Chilmark

This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience.

Abutting over 200 acres of protected conservation land of Menemsha Hills, the property enjoys a natural buffer along with direct access to scenic walking trails and some of Chilmark’s most iconic views. Ideally located just a short distance from Menemsha and Chilmark Center, it offers both seclusion and accessibility. Homeowners will also have access to Lucy Vinecent and Squibnocket beaches as Chilmark property owners.

With an established rental history and full winterization for year-round use, this home is well-suited for both personal enjoyment and income generation. For those seeking a foothold in one of Martha’s Vineyard’s most desirable towns, this is a compelling opportunity not to be missed.

First Floor

Entryway leads to the living room, Dining room, Kitchen with a smaller dining area, first-floor bathroom, Laundry, and utility closet.

Second Floor

Up the stairs leads to 4 Bedrooms and 3 bathrooms, with a deck off the Primary suite

Basement

Slab

Parking

Multiple spaces to park

Other Buildings

Detached Guest bedroom with full bathroom and Kitchenette. Garage attached to the guest quarters.

Second Dwelling

Detached bedroom with full bath, a dining area, and a small kitchen area.