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.

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40 Wintergreen Way, Chilmark

$ 1,100,000
Charming Chilmark getaway on 3 acres tucked off Middle Road. As you enter you are immediately aware that this home is built with quality and integrity throughout. Built by South Mountain, the home fea [more]
Charming Chilmark getaway on 3 acres tucked off Middle Road. As you enter you are immediat [more]
42 2,188 ft2full info
Sales

2 Rockrose Path, Chilmark

$ 1,695,000
This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of Meetinghouse Road in Chilmark. This heated, year round house is sited on one an [more]
This four bedroom, three bath home with ocean views and a private, south shore beach, is l [more]
43 2,100 ft2full info
Sales

345 North Road, Chilmark

$ 855,000
This classic Chilmark home offers 4 bedrooms, 3 fireplaces, 4 full baths plus outdoor shower on a lovely parcel with stonewalls and mature plantings. The living room and kitchen each have fireplaces, [more]
This classic Chilmark home offers 4 bedrooms, 3 fireplaces, 4 full baths plus outdoor show [more]
55 1,920 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

68 Meeting House Road, Chilmark

$ 1,725,000
Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019.
Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in cons [more]
43 2,300 ft2full info
Sales

277 North Road, Chilmark

$ 12,500,000
With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the isl [more]
With a sweeping entrance through an expansive farm field, walking and riding trails, woodl [more]
Sales

100 Beach Plum Lane, Chilmark

$ 8,500,000
Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. Th [more]
Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside c [more]
43 2,140 ft2full info
Sales

31 Tea Lane, Chilmark

$ 875,000
A beautiful site located in the hills of Chilmark right off historic Tea Lane. Convenient to both Chilmark and West Tisbury town centers and the beaches. Surrounded by stone walls and bordering by con [more]
A beautiful site located in the hills of Chilmark right off historic Tea Lane. Convenient [more]
Sales

55 Bijahs Way, Chilmark

$ 1,975,000
55 Bijah’s Way is a custom designed post and beam home built by well-known and respected island builder Heikki Soikkeli. Sited on 3 private acres, this home features 5 bedrooms, 4 ½ baths, screened po [more]
55 Bijah’s Way is a custom designed post and beam home built by well-known and respected i [more]
54.5 3,776 ft2full info
Sales

15 High Meadow Road-Lot 36, Chilmark

$ 675,000
This beautiful four acre lot in Chilmark is set on a gentle rise with vistas overlooking meadow and woodlands. The building site is open and filled with light. Peaceful and private, this lot abuts 184 [more]
This beautiful four acre lot in Chilmark is set on a gentle rise with vistas overlooking m [more]
Sales

252 Middle Road, Chilmark

$ 1,060,000
House and guest house on a hilltop sanctuary. The mid-century modern main house designed by Ronald Gourley offers open-living space with a glorious wall of windows that bring in dramatic light through [more]
House and guest house on a hilltop sanctuary. The mid-century modern main house designed b [more]
43 2,106 ft2full info
Sales

28 Black Point Road, Chilmark

$ 1,975,000
Bright and airy retreat on Black Point complete with key to Black Point Beach. Set on 5.4 acres off Black Point Road in Chilmark, this charming cottage brings an immediate feeling of peace and levity. [more]
Bright and airy retreat on Black Point complete with key to Black Point Beach. Set on 5.4 [more]
33 1,719 ft2full info

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