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

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

20 Tennis Lane, Chilmark

$ 2,195,000
A nicely appointed contemporary home in the center of Chilmark with 4 bedrooms and three bathrooms all newly renovated. This home has great entertaining spaces in and out. The large living room has a [more]
A nicely appointed contemporary home in the center of Chilmark with 4 bedrooms and three b [more]
43.5 2,673 ft2full info
Sales

46 South Ridge Road, Chilmark

$ 629,000
A stunning large building lot on the crest of a long knoll,overlooking the Tiasquam River Valley.Gently rolling terrain and a mix of deciduous ,evergreen and and hardwood trees at the end of a cul de [more]
A stunning large building lot on the crest of a long knoll,overlooking the Tiasquam River [more]
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

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

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

11 High Meadow, Chilmark

$ 749,000
This private three acre lot enjoys North shore waterviews, substantial building envelope, privacy from abutting Waskosim’s Rock Reservation, beautiful stonewalls, and pondviews. This is a rare o [more]
This private three acre lot enjoys North shore waterviews, substantial building envelope, [more]
Sales

135 State Road, Chilmark

$ 5,750,000
Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable d [more]
Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the [more]
41.5 2,300 ft2full info
Sales

15 Lake Road, Chilmark

$ 3,000,000
Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads… these are just some of the features of this extraordinary property ne [more]
Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centur [more]
52.5 1,927 ft2full info
Sales

46 South Ridge Road, Chilmark

$ 629,000
Lovely rolling land with dramatic sunsets and sweeping vistas of the Chilmark north shore.  Located in the desirable Meetinghouse Road Association which combines wonderful privacy, convenient Chilmark [more]
Lovely rolling land with dramatic sunsets and sweeping vistas of the Chilmark north shore. [more]
Sales

34 High Meadow Lane, Chilmark

$ 799,000
This four acre building lot off Old Farm Road offers an open, sunny building site on a knoll with waterviews of the Elizabeth Island and wooded land for another structure, a barn or walking trails on [more]
This four acre building lot off Old Farm Road offers an open, sunny building site on a kno [more]

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