139 Main Street, DowntownVineyard Haven, MA 02568Price: $3,750,000

Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses-now gracefully combined into a single half-acre parcel-this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming vestibule, it's clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal. Outside, the grounds feel secluded and mature-a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering afternoons in the dappled shade. A charming one-bedroom guest cottage sits tucked away from the main house, offering flexibility for guests, work-from-home, or rental income. This home has long been cherished by artists, collectors, and careful stewards-each adding their layer to the property's quiet patina. Just a short stroll to the ferry, shops, restaurants, library, and beach, 139 Main Street is a rare find: a truly in-town retreat that feels a world apart. This expansive main house offers flexible living with six rooms currently used as bedrooms, including a separate guest suite. The property has a 5-bedroom septic system per Title 5.