Fantastic investment opportunity in the highly desirable Bridgeport neighborhood, this meticulously maintained all-brick two-flat has been lovingly cared for by the same family for more than 30 years. Each spacious unit features 2 bedrooms and 1 full bath, with separate utilities and updated HVAC systems, while the first-floor unit offers the added convenience of in-unit laundry. The second-floor unit opens to a large private deck showcasing a spectacular Chicago skyline view, creating an exceptional space for entertaining or unwinding. A fully finished basement with an in-law kitchen and full bath adds valuable flexibility for extended family, guests, additional living space, or potential rental income. Outside, enjoy a full backyard and a two-car garage with a brand-new roof, along with new windows throughout the property. Above it all, the full unfinished attic offers exciting potential for future expansion. Located in the heart of Bridgeport, this property is just minutes from Chinatown, IIT, UIC, downtown Chicago, and major expressways. Enjoy convenient access to acclaimed restaurants, shopping, parks, public transportation, and the many new residential and mixed-use developments transforming the surrounding area. With its solid brick construction, prime location, skyline views, versatile finished basement, and substantial expansion potential, this property offers the perfect combination of income opportunity, long-term value, and Chicago lifestyle. A truly exceptional investment.