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
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, 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
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
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
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
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
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 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 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
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
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
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