3452 N Damen Avenue Welcome to one of Roscoe Village's most unique opportunities: a legal two-flat that lives like a single-family home. The opportunities are endless, also checking the box for a condo buyer, an owner-occupant, or the investor looking for a truly turnkey asset with a 5.7% cap rate. Situated within the highly coveted Audubon school boundaries, this home is set on a full 25125 lot, the home spans two levels plus a basement - all connected by both front and rear interior staircases, creating a natural sense of continuity while maintaining flexibility for evolving needs, The main level, Unit 1, greets you with vintage details and a sense of volume the moment you walk in, oversized windows flooding every room with natural light. Inside: hardwood flooring throughout, soaring ceilings, two bedrooms plus a third that serves beautifully as an office or guest space, a full bath, a spacious kitchen with a walk-in pantry and breakfast nook, and comfortable living and dining rooms. The second level, Unit 2, offers an expansive one-bedroom, one full-bath layout with a smart, dedicated office nook that can be converted to a second bedroom, and an ample storage closet spanning the length of the property. This flexible floor plan lends itself to a master suite, guest accommodations, or a standalone rental unit. The radiant-heated dug-out basement adds valuable bonus space with great ceiling height, and offers excellent functionality for play, work, fitness, hobbies, storage, or future finishing for extra living space or duplexing down unit 1. Step outside to a large, private yard that feels like your own personal retreat, complete with a two-car garage. Lovingly maintained with meaningful capital improvements completed within the last five years, including a newer roof, a mini-split heating/cooling system, a condenser, and additional system updates. Nestled at the heart of Roscoe Village, you are steps from the neighborhood's beloved restaurants, boutique shops, and coffee spots, including Volo, Le Sud, Starbucks, John's Place, Pilates and Coffee, Commonwealth, and Cinnamon Boutique. Enjoy weekend farmers markets, a stroll to Hamlin and Fellger Park, and easy access to the Brown Line for a seamless commute into the city. Whether you are looking to create your dream single-family home, have a condo alternative, owner-occupy one unit and rent the other, or land a strong investment with a 5.7% cap rate, the options here are truly endless. Do not miss this rare opportunity to own a home that truly has it all!