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!
Peaceful Chilmark three bedroom home offering privacy along with great proximity to both West Tisbury town center and Chilmark beaches. You will feel... Read More
Stunning, private, four and a half acre property set high atop shared driveway in Chilmark with association tennis court, dock and water access to pon... Read More
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This three bedroom beach house is in an idyllic location on Upper Chilmark Pond, offers direct pond access and the ocean (private ocean beach is direc... Read More
The historic Look House is located in Chilmark about a mile west of Beetlebung Corners. Built in the early 1900's (incorporating previous homes built ... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... 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
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
A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doo... Read More
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 water view property in Chilmark overlooking Quitsa Pond. Great water access with a private, shady path to Clam Point Cove. Exquisite sunset... Read More
Through the private gate, this home is set up on the hill with stunning views of Squibnocket Pond and the South Shore of the Atlantic. With endless wi... 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
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