1302 W Winona #3E, Chicago IL 60640

Stunning 2 bed + den, 2 bath penthouse in an all-brick contemporary newer construction building featuring a private rooftop deck, dedicated office/flex space, skyline views, and multiple outdoor living areas where Uptown meets Andersonville. Situated on a quiet tree-lined street, this thoughtfully upgraded home goes well beyond its original construction, offering exceptional storage, high-end finishes, and an ideal layout for both everyday living and entertaining. Flooded with natural light from north, south, and east exposures, the extra-wide open-concept living, dining, and kitchen space features wide-plank hardwood floors, oversized windows, a sleek gas fireplace, and seamless access to a private front balcony overlooking the tree-lined street below. The beautifully designed kitchen is anchored by a large quartz island and features Italian cabinetry, professional-grade stainless steel appliances, a built-in microwave convection oven, deep custom storage cabinetry, and not one, but two upgraded dishwashers with integrated water softeners. The spacious primary suite offers dual custom-organized walk-in closets and a spa-inspired bath with heated floors, dual vanities, and a Kohler Anthem three-function shower system. The generously sized second bedroom is complemented by a full guest bath, while the den provides the perfect work-from-home setup, studio, or flex space. Five custom-organized closets, an oversized laundry room with steam washer and dryer, an additional stainless steel refrigerator, and extensive storage throughout make this home as functional as it is beautiful. The private rooftop retreat is truly one of a kind, featuring new rooftop decking (2025), gas, water, sound, internet, cable, multiple seating and dining areas, a storage shed, and stunning skyline and treetop views. Direct access from the dedicated office/flex space creates a seamless indoor-outdoor living experience rarely found in the city. Additional improvements include a new A/C condenser (2024), UV light air purification system, and a rooftop storm door. Detached garage parking with storage area. Prime location between Uptown and Andersonville, with Edgewater just a short walk away, offering acclaimed restaurants, shopping, cafes, nightlife, the Berwyn Red Line, the lakefront, and countless neighborhood favorites right outside your door.