Chilmark Homes with Cape Style

Nestled on the enchanting island of Martha’s Vineyard, Chilmark is a picturesque town that embodies the charm of New England coastal living. Located in Dukes County, this serene haven is renowned for its stunning landscapes, rolling hills, and breathtaking ocean views. With its rich history and a close-knit community, Chilmark offers a unique blend of tranquility and vibrancy, making it a sought-after destination for those seeking both relaxation and adventure.

The homes in Chilmark often reflect the timeless elegance of Cape-style architecture, a quintessential New England design known for its gabled roofs and symmetrical facades. These charming residences harmoniously blend with the natural surroundings, featuring warm wood tones, inviting porches, and expansive windows that frame the island’s stunning vistas. Living in a Cape-style home in Chilmark means embracing the essence of coastal living, where sunsets over the Atlantic become part of your daily routine.

Chilmark is not just about beautiful homes; it’s also a gateway to outdoor adventures. With miles of pristine beaches, scenic hiking trails, and lush conservation areas, residents can immerse themselves in nature’s beauty while enjoying activities like fishing, kayaking, and birdwatching. The town’s rich cultural scene includes local art galleries, farmers' markets, and community events that foster a sense of belonging among residents.

Whether you are looking for a summer retreat or a year-round residence, Chilmark offers a unique opportunity to experience the best of island living. Discover the charm of Cape-style homes in this idyllic town and embrace a lifestyle filled with beauty, community, and endless adventure.

Newest Chilmark Homes with Cape Style

$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

$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

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