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
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
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with your morning coffee, a book or a glass of wine after a glorious day of exploring on the island of Martha's Vineyard. The quaint village of Menemsha is full of small quick bites, shopping, antiques, th
Chilmark 2019
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... Read More
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... 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
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
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around deck, association access to tennis. There is stunning south shore beach access as well. The home is a just a short distance to Chilmark center, Menemsha, and Lucy Vincent beach. Enjoy a day at Lucy Vin
Chilmark 2058
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around d... Read More
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around d... 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
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
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
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
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
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
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
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