1955 W Cortland Street # 3W

Rarely does a home combine architectural significance, exceptional outdoor living, and an unbeatable Bucktown location quite like this. Originally designed as the developer's personal residence, this extraordinary penthouse spans three levels and nearly 2,800 square feet, offering soaring ceilings, dramatic entertaining spaces, and three private outdoor retreats just one block from The 606 Trail. The moment you enter, you're greeted by a breathtaking two-story great room anchored by a dramatic wall of oversized arched windows that flood the home with natural light while framing peaceful views of the neighborhood's mature tree canopy. A floating staircase, contemporary fireplace, and gallery-like scale create a striking backdrop for both everyday living and effortless entertaining. The expansive open-concept layout flows seamlessly into the ArcLinea Convivium chef's kitchen designed for those who love to cook, gather, and entertain. Custom floor-to-ceiling cabinetry, integrated Subzero refrigeration, a commercial-grade stainless steel island, Miele and Gaggenaue appliances, and abundant storage combine beauty and functionality in equal measure. The upper level is dedicated to an extraordinary primary retreat that feels more like a boutique luxury hotel suite than a city condo. A private sitting area overlooks the living space below, while the spa-inspired bath features dual vanities, a steam shower, and an infinity soaking tub designed for relaxation. A custom walk-in closet and direct access to a private outdoor terrace complete the experience. Outdoor living reaches new heights with three separate private spaces that seamlessly extend the home's living and entertaining areas. Start your day on the front terrace overlooking Bucktown's picturesque tree-lined streets, complete with a gas line for effortless grilling, relax in the private hot tub lounge, or entertain under the city lights on the expansive rooftop deck, where breathtaking skyline views stretch for miles and additional gas connections provide exceptional flexibility for outdoor cooking, fire features, or future enhancements. An attached heated garage parking space with direct alley access and a private storage closet complete this rare offering, combining the comfort and convenience of a single-family home with the vibrancy of one of Chicago's most coveted neighborhoods. Additional highlights include Control4 smart home automation, integrated whole-home Bose audio, 27 zone controlled speakers throughout , dual-zoned HVAC with Nest thermostats, wine room, dedicated laundry room, extensive storage, and four included televisions currently integrated into the home's smart system. Recent improvements include refinished decks and pergola, new primary suite windows and terrace door, newly serviced steam system with access panel added, updated first-floor bath vanity, fresh interior paint, and new rooftop access doors. Located in a boutique self-managed six-unit building in the heart of Bucktown, steps from The 606, award-winning restaurants, neighborhood cafes, shopping, parks, and public transportation, this is a rare opportunity to own one of the neighborhood's most distinctive and architecturally compelling residences.