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
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 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
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
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
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
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hill location. Enjoy breathtaking water views from nearly every room and an ideal layout designed for both comfort and connection.
The main level features an open-concept kitchen, dining, and living are
Chilmark 2050
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hi... Read More
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hi... 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
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 comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offering plenty of privacy for the whole family. The Kitchen and Living Space span the top floor with deck access to enjoy the breezy summer nights. There are 2 outdoor showers with one directly off of the
Chilmark 2003
This comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offeri... Read More
This comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offeri... 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
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect for kids and fitness enthusiasts. The house is fully equipped with mini-split air conditioning and heating units throughout. It features spacious areas for gatherings, as well as cozy spots for enjoyi
Chilmark 2008
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect ... Read More
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect ... Read More
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupied.) Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond just a few short moments away. First floor has an open kitchen, dining and living room with f
Chilmark 2025
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupi... Read More
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupi... Read More
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