Chilmark Homes with Cape Style

Welcome to Chilmark, Massachusetts – a hidden gem nestled on the picturesque island of Martha’s Vineyard in Dukes County. Known for its breathtaking landscapes, serene beaches, and vibrant community, Chilmark offers a unique blend of natural beauty and rich history. With its rolling hills, rocky shorelines, and lush woodlands, this charming town is a haven for nature lovers and those seeking a tranquil retreat from the hustle and bustle of everyday life.

Chilmark is particularly renowned for its iconic Cape-style homes, which perfectly complement the coastal charm of the area. These classic New England residences feature steeply pitched roofs, symmetrical facades, and cozy interiors, creating an inviting atmosphere that feels like home. Many of these homes are set against stunning backdrops of the Atlantic Ocean or nestled within the serene woodlands, providing residents with breathtaking views and a sense of peace.

Living in Chilmark means embracing a lifestyle filled with outdoor adventures, from hiking the scenic trails of the nearby Menemsha Hills Reservation to enjoying a day at the pristine beaches of Lucy Vincent and Squibnocket. The town’s close-knit community is reflected in its local events, farmer's markets, and art galleries, making it easy to connect with neighbors and immerse yourself in the local culture.

Whether you’re looking for a summer getaway or a year-round residence, Chilmark’s Cape-style homes offer a perfect blend of comfort and charm. Discover the allure of this enchanting town, where every day feels like a vacation and the beauty of nature is just outside your doorstep. Welcome home to Chilmark!

Newest Chilmark Homes with Cape Style

$3,795,000

3 Beds ⋅ 4 Baths ⋅ 73545525 MLS

Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and tile.

96 Hammett Ln, Chilmark

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..

$4,995,000

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..

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.