Chilmark Homes with Cape Style

Welcome to Chilmark, a picturesque gem nestled in Dukes County, Massachusetts, where the charm of New England meets the serene beauty of coastal living. Known for its stunning landscapes, Chilmark offers a tranquil escape from the hustle and bustle of city life, making it a sought-after destination for those looking to embrace the idyllic lifestyle of Martha's Vineyard.

Chilmark is renowned for its stunning natural beauty, featuring rolling hills, pristine beaches, and a rich tapestry of wooded areas. Here, residents enjoy a close-knit community atmosphere with a variety of local events and activities, from farmer's markets to art shows. The region is also home to some of the most breathtaking views, particularly at the iconic Menemsha Hills, where hiking trails lead to panoramic vistas of the Atlantic Ocean.

When it comes to real estate, Chilmark is celebrated for its charming Cape-style homes. These classic residences, often adorned with shingle exteriors and inviting porches, perfectly capture the essence of coastal New England architecture. With their distinctive gabled roofs and cozy interiors, Cape-style homes provide both comfort and character, making them ideal for families and retirees alike. Many of these homes are situated on spacious lots, allowing for ample outdoor living space where residents can enjoy the stunning natural surroundings.

Whether you're seeking a peaceful retreat or a place to create lasting memories with family and friends, Chilmark offers a unique blend of coastal charm and community spirit. Discover your dream home in this enchanting region, where every day feels like a vacation.

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

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.

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