0 Bayberry Hill Rd, Cuttyhunk, MA 02713

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. 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.

Located just up the road from the village center, Bayberry Hill is sited on 1.09± ac of residential land. The residence and detached garage apt includes a combined 1,982± (measured) sq. ft.of living area with 4 bedrooms, 2 full baths and 2 half baths, an outdoor shower, and 3 fireplaces. Panoramic views of Buzzards Bay, Cuttyhunk Harbor, and Vineyard Sound are permanently preserved through a recent CR on the adjacent 11-acre parcel. Buyer will have deeded view easement rights over the 11-ac parcel to maintain current views per the reserved rights in the CR. Cuttyhunk Island, part of the Elizabeth Islands off the southern coast of Massachusetts is located between Buzzards Bay and Vineyard Sound. Just 550± acres with a year-round population of approx. 30 residents, the quaint island offers a quiet, beautiful, ocean environment perfect for fishing, sailing, reading and relaxing. The island’s population swells as summer residents, vacationers and boaters head over when the weather warms.