Step into refined living in this stunning Wicker Park duplex-up penthouse, set on an oversized lot on a quiet, tree-lined street. Designed for seamless indoor/outdoor living, this showstopping home features soaring 10' ceilings and 8' doors, polished concrete heated floors, in-ceiling Sonos surround sound, and an impressive wall of sliding glass doors that flood the space with natural light. The chef's kitchen is a dream, featuring a walnut live-edge island, Dekton countertops, an Artemide kitchen light fixture, Miele and Fisher & Paykel appliances, and abundant storage - all flowing effortlessly into the open living and dining areas, which open directly onto a spacious private deck -perfect for morning coffee or unwinding in the evening. The main level also includes a serene primary suite with a spa-inspired bath featuring a walk-in shower and soaking tub, along with a large walk-in closet. The home also includes a high-end steam humidifier system - an upgraded addition that enhances air quality and comfort year-round. Upstairs, you'll find three additional bedrooms with generous closet space and large windows, as well as a second family room with a custom built-in wet bar that spans the entire wall and serves as a true statement piece. Step outside to one of the home's most impressive features: a sprawling private rooftop oasis, built for entertaining. This outdoor retreat includes an electric pergola, built-in gas grill, two outdoor refrigerators, Paloform outdoor fireplace, Roca tiles, perimeter lighting, and an outdoor dog run (on both levels) - making it feel like your own private lounge in the heart of the city. The location offers easy access to Milwaukee, North Ave, Division, and is within walking distance to Wicker Park. You're also just steps from renowned restaurants, coffee shops, bakeries, the 606 Trail, CTA transit, and more. One garage parking space included-this is a rare opportunity to own a one-of-a-kind home designed for both comfort and style.