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!
33 properties available
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
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
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
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
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
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
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a private ocean beach just across the way. Imagine spending sunny days at Lucy Vincent Beach, only minutes down the shore! Tucked away at the end of a peaceful 1/4-mile dirt road, this property is convenie
Chilmark 2022
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a pri... Read More
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a pri... 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
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
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
Stunning water view property in Chilmark overlooking Quitsa Pond. Great water access with a private, shady path to Clam Point Cove. Exquisite sunsets and water views to Menemsha. Large parking area adjacent to the Pond. Spacious kitchen and dining room spills onto the large, elevated deck overlooking Quitsa Pond with additional dining and loung
Chilmark 2062
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
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
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, this home exudes unique character, while the open floor plan creates a light and inviting atmosphere. The fully equipped kitchen, dining area, and living area provide all the comforts of home. There are
Chilmark 2011
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
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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