Chilmark Homes with Ranch Style

Welcome to Chilmark, a picturesque gem nestled in the heart of Martha’s Vineyard, Massachusetts. Known for its stunning landscapes, serene beaches, and vibrant community, Chilmark offers an idyllic escape from the hustle and bustle of everyday life. This charming town, part of Dukes County, is characterized by its rolling hills, lush woodlands, and breathtaking coastline, making it a haven for nature lovers and outdoor enthusiasts alike.

Chilmark is not just a destination; it’s a lifestyle. With its quaint, rural ambiance, residents enjoy a strong sense of community while embracing the tranquility that comes with living in such a beautiful setting. The town boasts a rich history and a commitment to preserving its natural beauty, ensuring that Chilmark remains a peaceful retreat for generations to come.

When it comes to real estate, Chilmark features a variety of charming homes, with ranch-style properties being particularly popular. These single-story homes are designed for comfort and convenience, offering open floor plans that seamlessly blend indoor and outdoor living. Ranch-style homes in Chilmark often come with expansive yards, perfect for hosting summer barbecues or simply enjoying the serene surroundings. With their easy accessibility and thoughtful layouts, these homes are ideal for families, retirees, and anyone looking to embrace a relaxed coastal lifestyle.

Whether you’re seeking a permanent residence or a seasonal getaway, Chilmark’s ranch-style homes provide the perfect backdrop for creating lasting memories. Discover the beauty of Chilmark and find your dream home that embodies the essence of this charming coastal community.

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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