220 North Rd Chilmark MA 02535
$2,400,000 Main 4BR/3BA – Cottage 3BR/1BA
Welcome to 220 North Road Chilmark MA, 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.
Private patio off the main-house deck.
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. Send me more information about this Chilmark retreat
MAIN HOUSE Stone Fireplace, Cathedral Ceiling
You’re invited: Warm wood walls, hardwood floor, fireplace.
The rich wooden interior radiates warmth and relaxation and is enhanced by the living room’s floor-to-cathedral-ceiling natural stone fireplace.
Large, tree house-like deck makes for easy entertaining.
A large deck wraps around nearly half the house, giving you treehouse-like views and a magical setting for outdoor entertaining. Send me more information about the Main House & Guest Cottage
GUEST COTTAGE: intimate log-home
The guest cottage features intimate sleeping quarters.
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 guests will love.
A new, 3BR septic system was just installed (July 2026). Click here to request a showing
separate & independent
The path between main house & guest house maintains privacy.
Each house has its own septic system and well, making them truly separate and independent.
There’s room on the property for a swimming pool.
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. Click here to learn about Chilmark’s world-class beaches
Special considerations
Sail, kayak and paddle-board on nearby Quitsa Pond.
Ask about partial Seller financing.
Also, ask about Seller lease-back of the Guest Cottage which could significantly reduce the purchase price. Click here to request information about Seller Lease back of the Guest Cottage.
Nearby Golf Courses
Farm Neck Golf Club offers views of Sengekontacket Pond.
Martha’s Vineyard has five golf courses headed by Farm Neck Golf Club in Oak Bluffs. Favored by US presidents Bill Clinton and Barack Obama, this 18-hole championship layout is often ranked among the best public courses in New England and has earned a 4½ star rating in Golf Digest’s “Best Places to Play.” The club is about 14 miles and a half-hour away from 220 North Rd.
Just 18 minutes away is Mink Meadows Golf Club, a semi-private 9-holer that offers an ocean view and undulating fairways.
The private Vineyard Golf Club (11 miles, 20-25 minutes) is one of the most environmentally friendly courses in the world. Opened in 2002, it is entirely organic. Designed by Donald Steel and Tom Mackenzie, this 18-hole course features rolling fairways and natural fescue roughs.
Two other courses are the Royal and Ancient Chappaquidick Links (9 holes, public, quirky and fun (need to take Chappy ferry) and Edgartown Golf Club (private). Send me more information about this Chilmark property.
Key Features: 220 North Rd Chilmark MA
Main house: Dining room with views on three sides.
- House & Guest cottage on 3.00 private acres
- Main House: 4BR/3BA, 1,400 SF
- Guest Cottage: 3BR/1BA, 832 SF
- Main house: major renovation (2019)
- Bordered along rear property line by .66-acre conservation buffer
- Room for a swimming pool
- Main: Cathedral ceiling in great room w/ stone fireplace
- Main: Large deck, patio
- Main: Dramatic dining area
- Main: Boat shed
- Guest: new 3BR septic system
- Send me more information about this Chilmark property
Learn More about Chilmark, click here
About Chilmark, Martha’s Vineyard
Great Rock Bight beach: Walk from the property to the beach.
Noted for rolling hills, roaming wildlife, old stone walls and gorgeous coastline that create a scene straight out of a pastoral painting, Chilmark is a picturesque Up-Island town.
Settled in 1660, and made a separate township in 1694, Chilmark is now a mainly residential town, with lots of farming and a small working harbor that creates a haven for fishing and boating.
There are a number of sanctuaries in Chilmark including Menemsha Hills, 211 acres of land protected by the Trustees of the Reservation and crisscrossed with walking paths that allow hikers to enjoy wooded groves and breezy coastline.
Chilmark also has several lovely beaches, including the public Menemsha beach and two beaches open to permanent and summer residents only. Send me more information about this Chilmark house & guest cottage
Chilmark: Fisherman’s Haven
Although attractions like the Chilmark Store (pizza, sandwiches, sundries), the Chilmark library and the Chilmark Tavern are in more rural settings throughout the town; Menemsha is the real town establishment.
A quaint and picturesque fishing town along the Vineyard sound, Menemsha has long been a point of departure for draggers and lobstermen, as well as the site of the United States Coast Guard station. Send me more information about this Chilmark retreat
