Chilmark
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!
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
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
Pristine Chilmark secret! This beautifully appointed four bedroom including a guest house sits atop a secluded area for those that love nature and the... Read More
Lovely Chilmark home located on the North Shore tucked into a spacious wooded lot. This home offers great social space with a dining area off of the ... Read More
A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doo... Read More
Through the private gate, this home is set up on the hill with stunning views of Squibnocket Pond and the South Shore of the Atlantic. With endless wi... Read More
Vacation bliss awaits in this brand new four bedroom home with a pool in Chilmark. Enjoy the quiet luxury of Up-Island in this sophisticated contempor... 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
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. ( the estates main house is rented separately and may be occupi... 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
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 comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offeri... Read More
Tell us what you're looking for and someone will contact you with available options.
