Welcome to an impeccable treasure nestled in the heart of Oak Park.This incredibly maintained vintage 2-flat exudes elegance and charm, situated on a picturesque tree-lined street that perfectly complements the historic beauty of the neighborhood. The property offers two distinct living spaces, each thoughtfully designed to provide comfort and style. The bright and spacious first-floor unit includes 2 bedrooms, boasting an updated eat-in kitchen that's perfect for culinary adventures, a cozy working fireplace, pristine hardwood floors, and an updated bathroom with a luxurious walk-in shower and private front porch to relax. The second unit has a duplex layout that extends to the third floor, featuring a bedroom and bath on each floor. Primary has treetop views that adorn this beautiful street and a luxurious marble bath providing a serene backdrop for your everyday life. Beyond its aesthetic appeal, the home is rich in history and accolades, proudly recognized as a 2003 Cavalcade of Pride winner. Practical updates further enhance its allure, modern minisplits air-conditioning from 2020, efficient zoned heating and roof (2010). This residence also offers ample parking with a 2-car garage and 3 exterior spaces, ensuring convenience for you and your guests. The basement has been expertly dug out, providing the potential to be finished for additional living space, tailored to your personal needs and desires. Experience the perfect blend of vintage elegance and modern comfort in one of Oak Park's most coveted neighborhoods.