Dukes County · Massachusetts
Chilmark, MA Homes for Sale & Real Estate
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Chilmark spreads across the hilly, up-island part of Martha’s Vineyard, a landscape of stone walls, open fields and woods that drops down to the Atlantic and Vineyard Sound. Menemsha, its small fishing village, is known for its harbor, fish markets and sunsets. The town has a rural, agricultural feel, with farms, conservation land and winding roads.
Homes in Chilmark are often set on large lots: shingled farmhouses, contemporary homes with ocean views, cottages near Menemsha and seasonal properties among the hills. Island purchases, whether a year-round home or a summer place, come with their own questions, from conservation restrictions to rental rules, and Dolan O’Rourke can help you work through them.
Living in Chilmark
Menemsha fishing village
Menemsha’s harbor, fishing boats, seafood shacks and small public beach make this village a beloved island spot, especially at sunset.
Lucy Vincent Beach
Lucy Vincent Beach, with its clay cliffs and long stretch of sand on the Atlantic, is a well-known town beach.
Conservation land
Properties such as Waskosim’s Rock Reservation and Peaked Hill Reservation offer trails through woods and pasture with views across the island.
Farm country
Farms and farm stands throughout Chilmark, framed by stone walls and grazing land, keep the town’s rural landscape open and productive.
Dukes County · Massachusetts
Homes for sale in Chilmark, MA
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Getting around and the outdoors
Getting around
State Road, Middle Road and South Road connect Chilmark to West Tisbury and Aquinnah, and VTA buses serve the town. Ferries from Woods Hole and other ports reach Vineyard Haven and Oak Bluffs, and Martha’s Vineyard Airport offers flights to the mainland.
Parks and recreation
Menemsha Beach, Lucy Vincent Beach and Squibnocket offer swimming and sunset views, and Waskosim’s Rock and Peaked Hill reservations provide hiking with island views. Fishing from Menemsha, paddling the island’s ponds and cycling the hilly up-island roads are popular in summer.
Villages and neighborhoods in Chilmark
Nearby communities
Buying or selling in Chilmark?
Whether you are buying your first home, moving up, downsizing or investing, our agents will guide you from the first conversation to the closing table.
- Buyers: Learn about our Buyer Representation Services.
- Sellers: Explore our Seller Representation Services and flexible listing tiers.
- Home value: Find out what your Chilmark home is worth.
Client reviews
What our clients say
I had the absolute pleasure of working with John Dolan and Dolan O’Rourke Real Estate Services while selling my mother’s home. We were going through an extremely difficult transition. We were both unfamiliar with the process of selling a home. From day one, John made himself readily available and kindly explained every part of the process to my mother, always making sure she understood each detail. His knowledge and expertise goes far and above what we expected. His constant communication never left us guessing – we felt very involved in every part of the process. I was caring for my mother on my own and he did everything in his power to ease the burden of selling her property. John knew I had great anxiety over our difficult situation and would always tell me not to worry. He always found a resolution to every bump in the road- and now I am finally worry free! John made us feel cared for and safe. We cannot thank him enough for his hard work. He helped us find a deal that we never could’ve imagined and changed our life for the better!
John was amazing with helping us in our home buying journey! His knowledge and patience made things very easy for us as first time home buyers. I highly recommend John to anyone who wants professionalism and someone who’s gonna get the job done! Thanks John!
We worked with John of Dolan O’Rourke Real Estate Services to purchase our first home in the Greater Boston area. As first time home buyers, John invested a lot of time early on to educate us about what to expect and strategies to consider. Throughout the process John had great communication, listening and advice as we navigated a challenging market. John was approachable, knowledgeable and always fun to be around as we looked at numerous houses, and helped us shape our conversations to really dial in to what we were looking for. We would love to recommend John for future real estate services and are so appreciative of his hard work.
Thinking about buying or selling in Chilmark?
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