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!
30 properties available
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as recent renovations throughout further enhance an already beautiful spot - embracing the casual, carefree feeling within the calm, private serenity of up-island. The property offers six beautifully de
Chilmark 2064
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... Read More
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... Read More
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the updated kitchen and slider out to an upper deck with tree top views. Spacious living room to sprawl out with a large sectional sofa, perfect for relaxing after a day at one of the up-island beaches.
Chilmark 2079
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... Read More
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... 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
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
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
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
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
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cottage has 2 bedrooms on the first floor and 2 on the second floor. Enjoy the expansive deck along the entire back of the house and dine al-fresco. The open area dining, living and kitchen spaces are the
Chilmark 2002
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... 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
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
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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