Chilmark Homes with Ranch Style

Welcome to Chilmark, Massachusetts, a hidden gem nestled in Dukes County on the picturesque Martha's Vineyard. Known for its stunning landscapes, tranquil beaches, and charming rural atmosphere, Chilmark offers a unique blend of natural beauty and small-town charm. With its rolling hills, lush greenery, and breathtaking ocean views, this idyllic town is the perfect retreat for those seeking a peaceful lifestyle away from the hustle and bustle.

Chilmark is renowned for its commitment to preserving the environment and maintaining its quaint character. The town boasts a rich history, with quaint farms, art galleries, and local markets that reflect the essence of Vineyard life. Residents and visitors alike can enjoy outdoor activities such as hiking, fishing, and exploring the stunning coastline, making it a paradise for nature lovers.

For those considering a move to this enchanting town, Chilmark's ranch-style homes offer an appealing option. These single-story residences combine comfort and functionality, making them ideal for families, retirees, or anyone seeking a low-maintenance lifestyle. Ranch-style homes in Chilmark often feature open floor plans, spacious yards, and an abundance of natural light, allowing homeowners to enjoy the serene surroundings.

Living in a ranch-style home in Chilmark means embracing the beauty of the Vineyard while enjoying the convenience of modern living. With its welcoming community and stunning landscapes, Chilmark is more than just a place to live—it's a lifestyle. Discover your dream home in this charming town and experience the magic of Martha's Vineyard for yourself!

Newest Chilmark Homes with Ranch Style

$1,600,000

3 Beds ⋅ 3 Baths ⋅ 73546774 MLS

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 surrounding natural landscape. In addition there is a one bedroom one bath guest cottage. The property features extensive parking and serene, tree-lined privacy back from the main road, serving as a peaceful getaway, investment property or year-round island home. Bring your personal updates and creative touch or begin anew and make this classic Chilmark estate your very own island legacy.

132 South Rd, Chilmark

Listing courtesy of Listing Agent: Lisa Da Silva from Listing Office: Compass.

$1,300,000

2 Beds ⋅ 1 Baths ⋅ 73471152 MLS

Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available.

45 Quenames Rd, Chilmark

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$1,325,000

2 Beds ⋅ 1 Baths ⋅ 73471155 MLS

On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.

47 Quenames Rd, Chilmark

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

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