Set in the heart of Portsmouth on a storied stretch of Middle Street-lined with stately buildings and timeless architecture-this classic Italianate 5-unit multi-family is a rare gem. Just 0.5 miles from the vibrant West End and downtown, and located in the coveted Little Harbour neighborhood, this exceptional property is on the market for the first time in nearly 50 years. Lovingly maintained, the building features four spacious 1-bedroom, 1-bath units and a larger 2-bedroom, 1-bath top-floor residence. Each apartment offers tall ceilings, oversized windows, and generous room sizes, allowing for an abundance of natural light. Original woodwork, decorative fireplaces, and a grand front entryway highlight the craftsmanship of a bygone era, while the wrap-around front porch provides an inviting space to relax and take in the neighborhood charm. The home's Italianate style is evident in its tall, narrow windows, ornate woodwork, and symmetrical proportions-details that speak to the rich architectural heritage of the area. Granite hardscaping, brick sidewalks, and original front doors enhance its distinguished curb appeal. Whether you're an investor seeking a premier addition to your portfolio or envisioning a conversion into a stunning single-family residence or condos, this property offers unmatched character, flexibility, and location. Just a short stroll to downtown Portsmouth's shops, restaurants, and picturesque waterfront-opportunities like this seldom come along.