Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.