An exceptional opportunity to own a stunning penthouse duplex in the heart of Wicker Park, this impeccably designed 3-bedroom, 3-bathroom residence with additional den/office space, offers an elevated living experience complemented by an expansive private rooftop retreat. Nestled on a picturesque, tree-lined stretch of Le Moyne, the home spans three thoughtfully curated levels and features two distinct outdoor living spaces. This home is bathed in natural light through dramatic south-facing, floor-to-ceiling windows. The chef's kitchen is both refined and functional, showcasing sleek flat-panel white cabinetry accented by an espresso-finished peninsula, an oversized quartz island with breakfast bar seating, a built-in Sub-Zero refrigerator, and a premium Bosch stainless steel appliance suite. The open-concept living area impresses with soaring 19-foot ceilings, rich hardwood flooring, and freshly updated interiors throughout. Designed for both relaxation and entertaining, the home's outdoor spaces are truly extraordinary. The rooftop deck, which spans the full length of the property, was masterfully reimagined in 2019 with over $125K+ in bespoke enhancements, including a custom pergola, fully appointed outdoor kitchen, cedar privacy screening, automated irrigation planters, porcelain pavers with pedestal system, synthetic turf, and ambient LED lighting. A secondary rear deck, also upgraded in 2019, offers an additional $15K+ in improvements with a built-in grill and buffet. The serene primary suite provides a luxurious escape, complete with floor-to-ceiling custom built-in closets, and a spa-inspired bath featuring a deep soaking tub and a separate glass-enclosed shower. Generously sized second and third bedrooms are thoughtfully positioned, and both have incredible closet space. Additional features include pre-wiring for surround sound and security, one garage parking space, walk-in laundry / utility room with recently-upgraded washer/dryer, and a spacious storage unit. This boutique, two-unit building is self-managed and is ideally located just moments from the 606 Trail, as well as the vibrant dining, shopping, and nightlife of Bucktown and Wicker Park. The home also offers seamless access to I-90/94 and public transportation, delivering the perfect balance of tranquility and urban connectivity.