3248 N Oakley Avenue, Chicago IL 60618

Rare and exceptionally maintained legal four-unit in the heart of Roscoe Village and the highly sought-after Audubon School District, offering remarkable flexibility for owner-occupants, investors, or multi-generational living. Lovingly cared for by the same owner for more than 20 years, this unique property combines timeless architectural character, thoughtful updates, and an oversized lot with multiple outdoor and auxiliary living spaces. The owner's residence spans both the first and second floors, each offering 3 bedrooms, 1 bathroom, formal living and dining rooms, and impressive gas and wood-burning fireplaces. Rich in vintage charm, the home features beautifully preserved oak millwork, hardwood floors, stained-glass details, oversized windows, and generous room dimensions rarely found in today's construction. The renovated kitchen, completed in 2016, serves as the heart of the home with custom cabinetry, stone countertops, stainless steel appliances, and a large center island. A bathroom renovation completed in 2021 further enhances the living space. The garden apartment provides additional income potential and was recently occupied by long-term tenants of approximately seven years. The unit offers 2 bedrooms and 1 bathroom, a full kitchen, comfortable living space, and excellent storage. Previously configured as a 3-bedroom unit, part of the space is currently utilized for storage. Adding to the property's versatility is a substantial finished loft space above the detached garage, currently used as a fitness studio. The space is fully enclosed and benefits from existing plumbing infrastructure, offering flexibility for a home office, studio, gym, workshop, or future improvements. In addition to the detached garage, the oversized lot also includes a separate carport and generous outdoor space. Constructed with substantial limestone foundation walls measuring approximately 12 inches thick, the property reflects a level of craftsmanship and durability rarely seen today. Additional features include updated kitchens and baths, abundant storage throughout, separate outdoor spaces, and a detached garage with significant bonus space above. Ideally located on a picturesque tree-lined street in the heart of Roscoe Village, the property is just moments from neighborhood parks, local restaurants, boutique shopping, and everyday conveniences. Enjoy convenient access to the CTA Brown Line, multiple bus routes, and some of Chicago's most beloved North Side destinations while maintaining the quiet residential feel that makes this neighborhood so desirable. A rare opportunity to own a distinctive and well-maintained property with exceptional flexibility in one of Chicago's most sought-after neighborhoods.