Folly on Bayberry Hill

Perched high above the harbor on one of New England’s most secluded islands, Folly on Bayberry Hill is a classic Cuttyhunk retreat offering exceptional privacy, timeless coastal character, and sweeping panoramic water views. Located on Cuttyhunk Island in the Town of Gosnold, Massachusetts, the property overlooks Rhode Island Sound, Buzzards Bay, Cuttyhunk Harbor, and Vineyard Sound, capturing the beauty and simplicity of life in one of the Northeast’s last truly unspoiled island communities.

The home’s elevated setting creates a remarkable sense of openness, light, and connection to the surrounding coastal landscape. Inside, approximately 1,472 square feet of living space is filled with warm natural materials, sunlit interiors, and relaxed gathering spaces designed for effortless island living. The residence includes three bedrooms and two full bathrooms, with an additional upper-level finished living area offering flexibility for guests, workspace, or lounge space. An expansive wraparound deck and covered porch create seamless indoor/outdoor living and entertaining opportunities, while adjacent protected conservation land preserves the dramatic harbor views and provides direct access to extensive island hiking trails and open space.