1955 W Barry Street 2W Multiple offers received. Sunday open cancelled. Beautifully updated duplex-up in an intimate boutique building, offering the feel and functionality of a single-family home with low HOA dues and exceptional indoor-outdoor living. Perfectly positioned across from Hamlin Park, this move-in-ready residence combines designer finishes with thoughtful recent upgrades. The sun-filled main level features 9-foot ceilings, hardwood floors throughout, expansive living and dining spaces, and a private balcony overlooking the park. The open-concept, updated kitchen is designed for both everyday living and entertaining, featuring white cabinetry, quartz countertops, a Carrara marble backsplash, Viking stainless steel appliances, and abundant storage. Just off the kitchen, an additional bedroom offers excellent flexibility for guests, a home office, or playroom with a full bath on the level. The upper level offers two spacious bedrooms, including a luxurious primary suite with a custom California Closets walk-in closet and a spa-inspired bath complete with heated floors, a freestanding soaking tub, dual vanity, and separate glass-enclosed shower. A second-floor laundry room and generous closet space throughout add to the home's exceptional functionality. Another standout feature is the expansive 28' x 28' private rooftop terrace, thoughtfully designed for entertaining with composite decking, a pergola with built-in heater, outdoor television, turf for pets or play, and a dedicated gas line for easy grilling. Other recent improvements include a brand-new HVAC system with furnace and air conditioner, along with a new, beautifully updated fireplace. Directly across the street, Hamlin Park has recently completed an extensive renovation, including a new pool, resurfaced walking paths, new picnic areas, renovated tennis and basketball courts, and a newly added pickleball court, offering outstanding recreational amenities just outside your door. Complete with garage parking, designer finishes throughout, and an unbeatable Roscoe Village location close to neighborhood restaurants, shopping, and public transportation, this exceptional home offers luxury, convenience, and an incredible park-side lifestyle.