An unprecedented opportunity to own a premier piece of Down East history. Located in the heart of downtown Eastport, this 1887 Italianate treasure was designed by famed architect Henry Nelson Black. The building is well-preserved and maintained, balancing historic integrity with structural peace of mind. The ground floor features two highly visible storefronts offering unrivaled exposure in a thriving, walkable historic district. Characterized by soaring ceilings and expansive display windows, the retail spaces are anchored by two beloved local businesses. Boatload of Books, a vital year-round cultural anchor, provides immediate, reliable lease income. Sweeties Downeast, a famous regional confectionery destination drawing generations of visitors, is currently owned by the seller and is available for purchase separately, offering a turn-key business opportunity alongside the real estate. The building's upper level features a sprawling, open-concept luxury loft. Unobstructed, dramatic walls of windows frame jaw-dropping, direct ocean views of Passamaquoddy Bay, the Atlantic Ocean, and America's first sunrises. This spectacular loft includes a rare, spacious 3-bedroom, 2-bathroom owner's residence, sold completely turn-key and fully furnished, showcasing exceptional bespoke craftsmanship. It features custom millwork, tailored, one-of-a-kind furniture, artisanal lighting, and a premium chef's kitchen. Every element is built with purpose and designed to the exact dimensions of the room. With no stairs, direct street access, and ample parking, it is ready for immediate luxury living or high-yield vacation rental income. Whether you are looking for a multi-stream investment, a live-work setup, or a signature coastal holding with a thriving business acquisition option, this architectural masterpiece delivers unmatched prominence in Maine's historic waterfront city.