Chilmark
Chilmark is a small, rural community with most of its land devoted to residential and agricultural use. It boasts beautiful homes set on rolling hills, rambling stone walls, grazing sheep, and one of the most beautiful of all Vineyard drives: Middle Road. The center of town is quaint and is home to the Chilmark Community Center, library and town offices, the Chilmark Store and the Chilmark Tavern where you might spot a celebrity sitting in one of the rocking chairs on the porch enjoying a slice of pizza. Heading north from the town center is the little fishing village of Menemsha, arguably the best place to watch a sunset on the Vineyard. Fishing and charter boats are tied up on the dock where you can grab the freshest prepared seafood or the catch of the day at one of the fish markets. The Homeport Restaurant overlooks the harbor and there are galleries and shops lining the road to the beach. Menemsha Beach is open to the public and is on the calm water side of the island, parking fills fast so head there early. Lucy Vincent and Squibnocket Beach are on the south or surf side of the island and are reserved for town residents or their guests/renters only. These exclusive beaches alone are popular reasons to rent a home in Chilmark!
This four bedroom contemporary is the perfect up-island getaway just a mile from Lucy Vincent Beach, less than 2 miles to the Chilmark Store AND it in... Read More
Stunning views! From the moment you drive down the peaceful, semi-private driveway you sense the solitude and beauty of the surroundings. Located on e... Read More
Beautiful Chilmark with modern renovation located half a mile from the historical Menemsha Harbor. This reverse living home offers large open spaces a... Read More
A Chilmark cottage situated with privacy in a wooded area not too far from town beaches and Alley's General store. Enjoy peaceful mornings and evenin... Read More
Some of the most beautiful sunsets await you from the deck overlooking Menemsha pond and the ocean beyond. This Menemsha home offers not only some of ... Read More
Charming cottage and guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boat. The well stocked kitc... Read More
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around d... Read More
Lovely Chilmark home located on the North Shore tucked into a spacious wooded lot. This home offers great social space with a dining area off of the ... Read More
Escape to the tranquil town of Chilmark and enjoy the best of Martha's Vineyard with this charming single-level home. With a post-and-beam design, thi... Read More
Just a short distance down a charming up-island road, you will find this six bedroom estate, perfectly placed within it's surroundings, as if drawn o... Read More
Vacation bliss awaits in this brand new four bedroom home with a pool in Chilmark. Enjoy the quiet luxury of Up-Island in this sophisticated contempor... Read More
LOCATION LOCATION LOCATION! Embrace the charm of this charming 1950's cottage nestled in a prime up-island location, offering convenient access to nu... Read More
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