Rare opportunity to own a coveted penthouse loft in a sought-after Wicker Park building! Perfectly positioned at the corner of Division and Winchester, this sun-drenched home is steps from Wicker Park's best restaurants, cafes, boutiques, nightlife, and parks. Oversized corner windows on two exposures flood the space with natural light and showcase unobstructed neighborhood views, while soaring 12 foot ceilings, exposed brick, timber beams, newly refinished hardwood floors, and a real wood burning fireplace with gas starter create a modern yet warm loft aesthetic. The open concept living area is ideal for both everyday living and entertaining, while both bedrooms are fully enclosed. The updated white kitchen features stainless steel appliances, abundant storage, and timeless dark granite countertops. Unlike many newer buildings, this solid all-brick masonry loft is overbuilt by today's standards, offering exceptional privacy, quiet, and durability. Upstairs, enjoy a dedicated rooftop space - your own expansive section of the shared roof deck with plenty of room for outdoor dining, entertaining, and unforgettable summer gatherings with breathtaking skyline views. Additional highlights include large bedrooms, an updated ensuite primary bath, gas forced heat & central AC, and a generous storage unit. Best of all, this home includes an exceptionally rare two-car parking arrangement featuring one attached garage space plus a tandem exterior spot. This is city living at its finest!