33 Middle St, Gloucester, MA 01930

Built in 1853 and beautifully updated for todays lifestyle, the Obadiah Woodbury Home offers a rare chance to own a piece of Gloucesters history. Just steps to Stacey Boulevard, the Inner Harbor, restaurants, galleries, shops, beaches, and the MBTA, this stately in-town residence delivers coastal living with standout walkability. Inside are soaring ceilings, spacious rooms, classic moldings, and ornate fireplaces that honor its character, while a fully modernized kitchen adds everyday function. With a flexible layout and generous proportions, its ideal for multi-generation living. Recent upgrades include new roofing, full removal of knob-and-tube wiring, a state-of-the-art gas heating system with zones, and custom library shelving. The private yard is a rare in-town oasisperfect for entertaining, gardening, or quiet relaxation. Whether as a primary residence or second home, this gracious historic gem captures the best of Gloucester.