Chilmark
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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!
31 properties available
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 includes a key/access to private Black Point Beach. The home has distant views of the Atlantic, is privately situated on over three acres of land and is light and bright with lots of windows and warm wo
Chilmark 2077
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
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
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley kitchen, small dining table, comfortable queen sofa bed with updated mattress, and full bathroom. This cottage has two, small screened porches to enjoy the fresh air while taking in the serene natural
Chilmark 2053
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley k... Read More
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley k... Read More
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond Just moments away. Two spacious living rooms, front hall with grand staircase, dining room, s
Chilmark 2020
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, ... Read More
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, ... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cottage has 2 bedrooms on the first floor and 2 on the second floor. Enjoy the expansive deck along the entire back of the house and dine al-fresco. The open area dining, living and kitchen spaces are the
Chilmark 2002
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
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
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with your morning coffee, a book or a glass of wine after a glorious day of exploring on the island of Martha's Vineyard. The quaint village of Menemsha is full of small quick bites, shopping, antiques, th
Chilmark 2019
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... Read More
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... Read More
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to wander in the woods. Privacy, privacy, privacy offered on twenty two acres. Great space in the main house with five bedrooms on the main level and overflow off of the finished family room downstairs.
Chilmark 2060
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boat. The well stocked kitchen has everything you need for that lobster boil. Relax and eat on the outdoor deck and watch the sunset. Both houses, wonderfully decorated with antiques and top quality f
Chilmark 2068
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boa... Read More
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boa... 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 eight private acres in Upper Chilmark Pond, you are just a short boat ride or commute to the popular Lucy Vincent beach. Explore the ponds in a canoe, rowboat, or two man kayak. Relax on the spacious d
Chilmark 2014
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
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
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family and friends.
The house centers around a large kitchen, living, dining area that spills onto the expansive deck facing the ocean. Listen to the waves break from the primary bedroom suite with a private
Chilmark 2044
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family a... Read More
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family a... Read More
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Martha's Vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Fully renovated in 2022 with stunning views from almost every room. Enj
Chilmark 2021
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Mart... Read More
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Mart... Read More
Beautiful Chilmark with modern renovation located half a mile from the historical Menemsha Harbor. This reverse living home offers large open spaces and is the perfect vacation escape. The 3 bed 2 bath includes 2 Queen bedrooms that share a hall full bathroom and a main bedroom complete with a king bed and ensuite full bathroom. The upstairs open c
Chilmark 2056
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
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
Stunning, private, four and a half acre property set high atop shared driveway in Chilmark with association tennis court, dock and water access to pond and the private section of South Beach. This house is a nature's paradise, with over four acres of trails, large, spacious yard, outdoor shower and great outdoor patio space. Enjoy wonderful summer
Chilmark 2063
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
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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