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!
32 properties available
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the updated kitchen and slider out to an upper deck with tree top views. Spacious living room to sprawl out with a large sectional sofa, perfect for relaxing after a day at one of the up-island beaches.
Chilmark 2079
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... Read More
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... Read More
The historic "Look House", located in Chilmark about a mile west of Beetlebung Corner. Originally built in the early 1900's (incorporating previous homes built in the mid-1800's), it has been completely remodeled and the historic character kept with updates completed to suit modern comforts and conveniences. Galley kitchen, living room, and dining
Chilmark 2009
The historic "Look House", located in Chilmark about a mile west of Beetlebung Corner. Originally built in the early 1900's (incorporating previous ho... Read More
The historic "Look House", located in Chilmark about a mile west of Beetlebung Corner. Originally built in the early 1900's (incorporating previous ho... 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
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
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
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
LOCATION LOCATION LOCATION!
Embrace the charm of this charming 1950's cottage nestled in a prime up-island location, offering convenient access to numerous private Chilmark beaches with town permits. The open kitchen boasts new granite countertops and refinished cabinets, seamlessly connecting to the inviting living room. Additional storage is ava
Chilmark 2054
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
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
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
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
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as recent renovations throughout further enhance an already beautiful spot - embracing the casual, carefree feeling within the calm, private serenity of up-island. The property offers six beautifully de
Chilmark 2064
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... Read More
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... 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 on the page. A modern farmhouse with a sophisticated décor, a coalescence of mid-century modern, industrial and antique furnishings. Comfortable living spaces share a see-through gas fireplace, gourmet
Chilmark 2010
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
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
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. This 4300 sq. ft. haven grants you exclusive access to the pristine Quansoo Beach, a private association beach of unparalleled beauty. Additionally, the opportunity to purchase passes for any of Chilma
Chilmark 2017
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. T... Read More
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. T... Read More
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