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

42 South Ridge Road, Chilmark

$ 1,850,000
A special opportunity for a hill top post and beam with stunning sunset views across the Chilmark Valleys. Built in 2002 by Yankee Barn, this well constructed, spacious and bright home was designed as [more]
A special opportunity for a hill top post and beam with stunning sunset views across the C [more]
42.5 3,951 ft2full info
Sales

42 South Ridge Road, Chilmark

$ 1,850,000
Spectacular post and beam home set among rolling Chilmark hills. This house sits beautifully on the land and is tucked into two knolls. The pastoral views are endless. Gaze out the large window wall a [more]
Spectacular post and beam home set among rolling Chilmark hills. This house sits beautiful [more]
42.5 3,951 ft2full info
Sales

0 Beach lot Quansoo, Chilmark

$ 320,000
Quansoo beach lot on Chilmark’s South Shore. Private access this gorgeous iconic sandy beach, perfect for swimming, surfing, fishing, and beach walks or launch your paddleboard and kayak in the [more]
Quansoo beach lot on Chilmark’s South Shore. Private access this gorgeous iconic san [more]
Sales

260 South Road, Chilmark

$ 4,195,000
Waterview Chilmark estate sprawling over 6.1 acres with access to Chilmark Pond and an Atlantic Ocean beach. Known as The James Allen House, this historic home has been lovingly maintained by the same [more]
Waterview Chilmark estate sprawling over 6.1 acres with access to Chilmark Pond and an Atl [more]
63 2,604 ft2full info
Sales

0 Beach Lot Quansoo, Chilmark

$ 315,000
Spectacular south shore beach lot. Enjoy beautiful summer days on this private, Quansoo Beach. Ownership provides deeded access to one of the most desirable beaches on Martha’s Vineyard. Swim, f [more]
Spectacular south shore beach lot. Enjoy beautiful summer days on this private, Quansoo Be [more]
Sales

11 High Meadow, Chilmark

$ 699,000
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

96 Hammett Lane, Chilmark

$ 659,000
A beautiful 4.2-acre piece of land at the top of Hammett Lane. This is a very special spot with gently undulating woodlands punctuated by lichen-covered boulders. The property can support 6 bedrooms, [more]
A beautiful 4.2-acre piece of land at the top of Hammett Lane. This is a very special spot [more]
Sales

4 Peases Point Way, Chilmark

$ 849,000
Located down an idyllic country lane, this beautiful 3 bedroom home offers an inviting open floor plan with cathedral beamed ceilings perfect for entering summer family and friends. Renovated in 2004, [more]
Located down an idyllic country lane, this beautiful 3 bedroom home offers an inviting ope [more]
32.5 1,652 ft2full info
Sales

11 Azalea Lane, Chilmark

$ 5,200,000
With 425 ft of private ocean beach, this offering deserves its reputation as the “ultimate beach house”. The 5-bedroom home has been completely renovated to the highest specifications with [more]
With 425 ft of private ocean beach, this offering deserves its reputation as the “ul [more]
54.5 3,750 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]

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