Chilmark

Chilmark is up-Island and it feels it — rolling hills, stone walls, and long views over open pasture to the water. Menemsha, its fishing village, still lands catch commercially and draws a crowd every evening for the sunset off the jetty. Homes for sale in Chilmark sit on large lots with real distance between them; there is no commercial centre beyond Beetlebung Corner and the Menemsha docks, and for most buyers that is the point. The south shore takes in Squibnocket and Lucy Vincent Beach, both restricted in season to town residents and their guests, which is a material part of what is being bought. Chilmark holds the least inventory of any town on the Island and some of its highest values.

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48 listings

8 Snail Road, Chilmark

$15,400,000

8 Snail Road, Chilmark

6 beds | 7 baths | 6,967 sq ft

44 Cencelle, Chilmark

$5,295,000

44 Cencelle, Chilmark

4 beds | 3 baths | 3,432 sq ft

Data last updated: 07/26/2026. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.© 2026 LINK, All Rights Reserved. LINK does not warrant the accuracy, reliability or completeness of this information.