Rarely available penthouse duplex in one of Old Town's most architecturally captivating homes, located in the iconic St. Michael's High School building. This one-of-a-kind loft features 16-foot ceilings, exposed brick, and large sun-drenched windows offering sensational tree-top views. The expansive, open floor plan spans 4,200 square feet with wonderful detail throughout. The main level showcases a cathedral-style living and dining area that flows effortlessly into the expansive kitchen, equipped with top-of-the-line appliances, abundant counter space, and a private balcony that extends off the kitchen. The main floor also features an additional living space great as a den or family room, a newly designed powder room, and one of the four bedrooms. The top floor includes three spacious bedrooms, with skylights of cathedral views, along with two new bathrooms. The all marble primary bathroom has been completely renovated, featuring marble radiant heated floors, a freestanding tub, and an extra-large shower. The building is exceptional and has a newly renovated elevator, lobby, and elegant common areas. It also features two outdoor common spaces, including a fantastic new rooftop deck with grills and 360-degree, unobstructed city views. Additionally, there is a spacious, landscaped terrace with a deck, perfect for hosting large gatherings or collaborations with neighbors. The home includes two attached, heated garage parking spaces and one storage locker (can rent additional for 50/month). Situated in this prime Old Town location, you'll enjoy close proximity to Lake Michigan, Wells St., Armitage, Lincoln Park Zoo, North Ave Beach, the farmers market, and a wide range of excellent restaurants and shops. Lincoln Elementary and High Schools are nearby, and there's easy access to public transit!