Charming and well-maintained Legal 2-flat in the heart of Roscoe Village/Lake View, just half a block from the vibrant Southport Corridor and walking distance to Wrigley Field, theaters, parks, shopping, and restaurants. Unit 1 offers 2BD plus additional office/bedroom space, 1 full bath, original oak woodwork and doors, a double closet in the main bedroom, a laundry chute, and glass shelves in the dining room. The main bedroom has brand new carpet. Unit 2 features 3BD/1BA, showcasing original oak woodwork, doors, and a built-in dining room hutch. There are high ceilings and large windows throughout. The basement is clean and unfinished with approximately 7ft ceilings. This property features a 7-year-old roof, a shared washer/dryer in the basement, back porches and stairs replaced in 2005, and a garage resided in 2018 with new windows and gutters. Tuck-pointing was completed in 2020 and 2022. This home is located in the sought-after Hamilton School District. It is an excellent opportunity for investors or owner-occupants to own a character-filled property in one of Chicago's most desirable neighborhoods.