Chilmark Real Estate

Nestled on the picturesque island of Martha's Vineyard, Chilmark is a hidden gem in Dukes County, Massachusetts. Known for its serene landscapes and charming New England character, this quaint town offers a perfect blend of natural beauty and rich history. With its rolling hills, stunning coastline, and lush woodlands, Chilmark is a haven for outdoor enthusiasts and those seeking tranquility.

Chilmark is renowned for its pristine beaches, including the breathtaking Menemsha Beach, where you can watch the sun dip below the horizon in a blaze of colors. The town’s commitment to preserving its natural beauty is evident in its conservation efforts, ensuring that residents and visitors alike can enjoy the unspoiled landscapes. The area is also home to some of the island's finest hiking trails, perfect for exploring the diverse flora and fauna that thrive in this coastal paradise.

Culturally rich, Chilmark boasts a vibrant community, with local art galleries, farmers' markets, and seasonal events that celebrate the island's heritage. The town's historic charm is reflected in its well-preserved architecture, from classic New England homes to quaint cottages that exude warmth and character.

For those considering a move to this enchanting area, Chilmark offers a unique lifestyle that balances the tranquility of nature with the vibrancy of community life. Whether you’re seeking a summer retreat or a permanent residence, Chilmark is a place where memories are made, and the beauty of New England shines through in every season. Discover the allure of Chilmark, where every day feels like a getaway!

Newest Listings in Chilmark

$2,250,000

4 Beds ⋅ 3 Baths ⋅ 73555055 MLS

21 & 25 Fulling Mill Road, Chilmark

Listing courtesy of Listing Agent: Jessica Holtham from Listing Office: Wallace & Co. Sotheby's International Realty.

$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.

$15,400,000

6 Beds ⋅ 9 Baths ⋅ 73538291 MLS

Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$5,400,000

3 Beds ⋅ 2 Baths ⋅ 73531359 MLS

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$5,350,000

4 Beds ⋅ 5 Baths ⋅ 73495595 MLS

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

205 South Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$7,350,000

4 Beds ⋅ 5 Baths ⋅ 73478310 MLS

Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.

308 South Road, Chilmark

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.

$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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