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
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
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
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
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
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
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 beautiful combination of old and new awaits you in this lovingly restored eighteenth century farmhouse. Throughout the home you will find wonderful pieces of history from the island and beyond, while the owners have updated all systems to the twenty first century standards. Central air, updated baths, and modern kitchen appliances make for a luxu
Chilmark 2005
A beautiful combination of old and new awaits you in this lovingly restored eighteenth century farmhouse. Throughout the home you will find wonderful ... Read More
A beautiful combination of old and new awaits you in this lovingly restored eighteenth century farmhouse. Throughout the home you will find wonderful ... 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
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
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
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
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
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