Originally built by a prosperous Scottish merchant, George Robertson c.1855, 34 Smith Street is an Italianate-style masonry residence that blends architectural grandeur with income-producing versatility. Offered on the open market for the first time in 70 years, this property presents a once in a generation opportunity for an end user or an investor in a prime downtown location. Rich in history and encompassing approximately 12,500 square feet on an expansive .59-acre corner lot, this historic estate offers a rare combination of scale, location, and potential in one of Charleston's most sought-after neighborhoods, Harleston Village.The stately three-story façade is complemented by two south-facing piazzas, offering an inviting place to relax or entertain while overlooking beautifully landscaped grounds. Soaring ceilings, original hardwood floors, and intricate plaster moldings represent the home's enduring interior elegance. The main floor's formal parlor and dining rooms showcase period light fixtures, marble fireplaces, and large pocket doors, illustrating mid-19th century-era craftsmanship at its finest. Historical photos show formal gardens adorned with expansive yards, one of the largest parcels in the entire Harleston Village neighborhood. This grand home is currently configured with ample living space for the owners on the main floor and second floor. In addition, there are 9 total rental units, which include four apartments within the primary residence, four in the historic two-story dependency, and a one-bedroom carriage house apartment. The property offers 14 dedicated off-street parking spaces, a rare amenity in downtown Charleston, and tenants in place with leases that run month to month. This property presents numerous possibilities: restore the entire property into a grand single-family residence, maintain the existing multifamily configuration, or create a blend of private residence and supplemental rental income. 34 Smith Street is more than a homeit is a legacy property, steeped in history and poised for its next chapter and next owner. No easements have been placed on this property and its one property you do not want to miss seeing!