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!
30 properties available
This unique four-bedroom converted barn in Windy Gates offers a large open first floor with kitchen, dining and living space. Original barn doors open to outdoor patio seating and let the natural light pour in. All four bedrooms are on the second floor with one half bathroom. The only full bathroom with a shower at the bottom of the stairs on the f
Chilmark 2071
This unique four-bedroom converted barn in Windy Gates offers a large open first floor with kitchen, dining and living space. Original barn doors open... Read More
This unique four-bedroom converted barn in Windy Gates offers a large open first floor with kitchen, dining and living space. Original barn doors open... Read More
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful South Shore of the Atlantic. Large windows fill the space with natural light, while expansive decks invite you to relax and soak up the sun. With five spacious bedrooms and five luxurious bathrooms, th
Chilmark 2073
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful S... Read More
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful S... Read More
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views and Menemsha Pond vistas featuring spectacular sunsets. This well-maintained single-story home boasts 4 bedrooms, two and a half bathrooms, and a wonderful open living/dining/kitchen plan. There are ca
Chilmark 2085
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views a... Read More
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views a... Read More
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary retreat. Lounge by the pool, dine outdoors, and sleep peacefully in one of the Thuma beds. The main floor offers open-concept living, dining and kitchen spaces with grand vaulted ceilings anchored by
Chilmark 2001
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... Read More
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... 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 the best views the island has to offer, but is minuets to Menemsha village, with its' artisans shops, and beaches. This property includes the main house, along with a spacious guest house with a queen
Chilmark 2061
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
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
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
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
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
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
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
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
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