Live in Historic Luxury in the Heart of the Gold Coast. Located on a quiet, tree-lined stretch of Division Street, this sun-filled two-story penthouse offers the perfect combination of vintage character and modern living in one of Chicago's most desirable neighborhoods. This 3-bedroom, 3-bathroom duplex-up condo is situated in an intimate 2-unit building and showcases timeless architectural details like original millwork, soaring ceilings, and hardwood floors throughout the living area (and under the carpet on the staircase) with opportunity for personalization. Step into a dedicated entry foyer that offers a warm welcome and separation from the main living spaces-ideal for added privacy and everyday functionality. The thoughtfully renovated kitchen features custom cabinetry, a breakfast bar, and high-end stainless appliances, perfect for both daily life and entertaining. The open, airy layout includes a bright living space with a wall of windows, gas fireplace, and generous space for multiple seating areas. On the main level, you'll find the primary suite with a private bath, a spacious second bedroom, a full guest bath, abundant closets, and in-unit laundry. A beautifully carved wood staircase leads to the upper level, where a flexible third bedroom with en suite bath and walk-in closet-currently used as a family room-opens to two private outdoor spaces. Enjoy your own rooftop retreat with a 650 sq ft deck complete with planters, gas line, and room for lounging, dining, or gardening-plus views of the lake and Gold Coast buildings. All just steps from Oak Street Beach, the Magnificent Mile, world-class dining, shopping, and transit. This unique, move-in ready penthouse offers a rare opportunity to own a piece of Gold Coast luxury real estate with outdoor living, vintage elegance, and modern comfort with room to make it your own. Rental garage parking next door and across the street. Contact listing agents for additional parking details.