Classic Roscoe Village legal two-flat with additional third-floor in-law/flex space, offering exceptional versatility for investors, owner-occupants, or those considering a single-family conversion. The owner's duplex-down residence features four bedrooms and three bathrooms and offers an open-concept kitchen and family room, a separate formal dining room, and multiple living and entertaining spaces highlighted by a cozy fireplace. The spacious kitchen includes abundant cabinetry, granite countertops, a center island, walk-in pantry, and additional space ideal for casual dining, a playroom, or den. Generously sized bedrooms provide ample closet space, complemented by additional storage throughout the home, and a full-size in-unit washer and dryer. The bright and well-maintained second-floor unit offers two bedrooms and one bathroom, an additional bonus room, and is currently leased, providing immediate rental income. The unit features an updated kitchen with quartz countertops and an island, as well as an updated bath and a full-size in-unit washer and dryer. Water and garbage included in the monthly rent. In addition to the legal two-flat configuration, the property includes a finished third-floor non-conforming in-law/flex space with three rooms, separate front and rear access, and a refrigerator only (no other kitchen appliances). The space offers flexibility for extended living, workspace, guest accommodations, or future rental potential. Buyers should conduct their own due diligence regarding permitted uses. Additional features include a rear deck, large private backyard, and a two-car detached garage. Located on a quiet tree-lined street within the highly regarded Audubon School attendance area; this property is an easy walk to the seventy-seven bus and Brown Line stations at Paulina, Addison，and Southport. Enjoy convenient access to Roscoe Village dining，coffee shops，boutiques，neighborhood events，the Southport Corridor，Wrigleyville，and North Center amenities. Rare opportunity to own a legal two-flat with additional finished in-law/flex space in one of Chicago's most desirable neighborhoods.