Just blocks from the vibrant Roseway Business District - home to neighborhood favorites like Mom & Pop Wine Shop, Pizzaria Otto, Burrito Azteca, ReRun, and more - this stately Craftsman presents a rare opportunity for investors, owner-occupants, or those seeking flexible multigenerational living. Currently configured as a legal triplex, the property also offers the unique ability to combine the two upper units into a single residence. Recent updates include beautifully refinished hardwood floors, new carpet, and fresh interior paint throughout. The main-floor residence lives large, featuring an elegant formal living room and dining room, a spacious kitchen, a versatile den, a generously sized bedroom, and a hall bath complete with a classic clawfoot tub. Abundant natural light fills the home, while the welcoming front porch provides the perfect place to relax and enjoy the neighborhood. Accessed by a private exterior staircase, the upper-level unit opens to a spacious foyer and includes a bright living room, two bedrooms, and an updated kitchenette. Downstairs, the expansive lower-level unit offers durable plank flooring, a large open-concept kitchen and living area, and one bedroom. Outside, you'll find ample space for gardening, entertaining, and off-street parking thanks to the oversized rear parking pad and patio area. Whether you're looking for rental income, a place to put down roots with extended family, or a combination of both, this exceptional Roseway property offers endless possibilities.