Chilmark

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 on Martha’s Vineyard.

Sales

114 Middle Road, Chilmark

$ 2,250,000
New Price! This masterfully-crafted home completed in 2010 was built with the highest quality materials, finishes, and mechanics. There is custom paneling, mill work, and cabinetry gracing each and ev [more]
New Price! This masterfully-crafted home completed in 2010 was built with the highest qual [more]
33.5 3,951 ft2full info
Sales

21 Squibnocket Road, Chilmark

$ 4,375,000
Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated wit [more]
Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach h [more]
42.5 2,018 ft2full info
Sales

22 Quitsa Lane, Chilmark

$ 9,995,000
Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha’s Vineyard. This home is full of character with access to private beac [more]
Spectacular and charming; this cottage style home and guest annex is located in one of the [more]
64.5 3,888 ft2full info
Sales

61 Stonewall Road, Chilmark

$ 2,500,000
Stonewall Association, one of the premier waterfront neighborhoods in Chilmark, is the location of this brilliant renovation. A wall of beautiful windows across the entire length of the house, white t [more]
Stonewall Association, one of the premier waterfront neighborhoods in Chilmark, is the loc [more]
43 2,537 ft2full info
Sales

1 Azalea Lane, Chilmark

$ 8,250,000
Rarest of the rare – Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for [more]
Rarest of the rare – Ocean-view Chilmark home with swimming pool, 440 feet of privat [more]
53.5 2,511 ft2full info
Sales

95 Stonewall Road, Chilmark

$ 14,850,000
Paradise is located at the magical intersection of the Atlantic Ocean and Stonewall Pond. A true seaside retreat, this 4-acre property with main house and guesthouse welcomes you to an enchanted life. [more]
Paradise is located at the magical intersection of the Atlantic Ocean and Stonewall Pond. [more]
65.5 3,008 ft2full info
Sales

51 State Road, Chilmark

$ 1,200,000
Walk to Town, Library and Chilmark Store from this newly built classic Vineyard Colonial situated in a peaceful serene setting with established plantings that provide plenty of privacy all around. 3 b [more]
Walk to Town, Library and Chilmark Store from this newly built classic Vineyard Colonial s [more]
34 2,600 ft2full info
Sales

31 Tea Lane, Chilmark

$ 875,000
Through a break in the ancient stone wall a meandering driveway leads you to this beautiful hillside site surrounded by old stone walls and bordering conservation land. A mix of ancient oaks, beech an [more]
Through a break in the ancient stone wall a meandering driveway leads you to this beautifu [more]
Sales

18 Spruce Gate Road, Chilmark

$ 7,500,000
The best and most coveted location on Martha’s Vineyard – Squibnocket Farm. Set within a private, gated +/- 500 acre community that includes over 300 acres of conservation land, extensive privat [more]
The best and most coveted location on Martha’s Vineyard – Squibnocket Farm. Set with [more]
53.5 3,700 ft2full info
Sales

20 Tennis Lane, Chilmark

$ 2,195,000
A thoughtfully appointed contemporary home in the center of Chilmark with 4 bedrooms and three and a half bathrooms all of which are newly renovated. This home has great entertaining spaces in and out [more]
A thoughtfully appointed contemporary home in the center of Chilmark with 4 bedrooms and t [more]
43.5 2,673 ft2full info
Sales

6 Post Oak Road, Chilmark

$ 2,950,000
Rare Opportunity to Own One of The Nicest Winterized Homes in Chilmark. This House Has It All, And Could Either Be a Great Income Property Or a Great Place to Call Home. 5 Bedrooms, 4 Full Bathrooms ( [more]
Rare Opportunity to Own One of The Nicest Winterized Homes in Chilmark. This House Has It [more]
55 4,332 ft2full info

Compare Listings