Chilmark, MA Houses for Sale under $2,000,000

Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

Valene Pires The Agency

Historic West Tisbury farmhouse with detached guest cottage on 1.27 acres in the heart of West Tisbury. Just moments from Alley's General Store, 7a Foods, North Tisbury Village, and a short drive to beaches and both up- and downd Island destinations. This property presents a rare opportunity for a family compound, multi-generational living, or investment with rental income potential. The

Emma Bryant Studio Realty

House & Guesthouse near Long Point Beach! The Island's coveted south shore is minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet garden, storage shed, and outdoor shower. Inside is open with natural light from

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spacious deck. The first-floor primary suite offers two en-suite baths and two walk-in closets, while

Sheila Morse Island Real Estate

Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the

Julianna Flanders Flanders Real Estate

Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

Lisa Da Silva Compass

A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

Sheila Morse Island Real Estate