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CHILMARK

345 North Road, Chilmark, MA 02535

Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$1,375,000.00
Listed: 20th April, 2026
Listed Price: $1,550,000
Contingent: 22nd September, 2026
Back on Market: 1st October, 2026
Price change: 25th August, 2026
New Price: ↓ $1,375,000
LINK ID: 44126
STATUS: AVAILABLE
Bedrooms: 5
Baths: 5
Rooms: 11
Living Space: 2266
Acreage: 0.5000
Water Frontage: None

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Outdoor Spaces: Beach Access - Public, Deck, Patio
Features: Insulation, MiniSplit, Outdoor Shower, WdStove
Year Built: 1981
Second Dwelling: Existing Second Dwelling
Zoning: RES
Water: Well
Sewer: Septic Tank
Lead Paint: Unknown
Foundation : Concrete Slab
Heat: Heat Pump
Fireplaces: 3
Yard Type: Yes
Flooring: Bamboo
Stove: Yes
Washer: Yes
TV: Cable

DESCRIPTION

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

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

THIRD FLOOR DESCRIPTION
N/A

BASEMENT DESCRIPTION
Slab

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

SECOND DWELLING
Existing Second Dwelling

PARKING
Multiple spaces to park
Martha's Vineyard - Island Wide Listings - Updated 21st of October, 2026
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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals
PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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