Spacious and beautifully updated 5-bedroom, 3-bath duplex-down in the highly sought-after Woodlawn neighborhood, just minutes from public transportation, the University of Chicago, and the future Obama Presidential Center. Offering exceptional space and flexibility, this home is ideal for homeowners, multigenerational living, or investors seeking additional income potential. The main level features refinished hardwood floors (2024), fresh paint throughout, and a bright open-concept layout designed for comfortable living and entertaining. The sun-filled living room showcases a cozy fireplace and Juliet balcony, flowing seamlessly into the updated kitchen with granite countertops, custom cabinetry, breakfast bar, and newer stainless-steel appliances, including a refrigerator and dishwasher (2024). Three generously sized bedrooms are located on the main level, including a spacious primary suite featuring a spa-inspired bath with dual vanity, jacuzzi tub, and separate shower. Step outside to your private terrace and enjoy the convenience of an assigned parking space. The fully finished lower level expands the living space with a large recreation room complete with a wet bar, two additional bedrooms, and a full bathroom featuring dual sinks, a soaker tub, and separate shower. This level also includes a second kitchen with a newer cooktop and refrigerator (2024), washer and dryer, and a private entrance, creating an ideal setup for extended family, guests, or related living arrangements. Don't miss this unique opportunity to own a versatile and well-maintained home in one of Chicago's fastest-growing communities. Property is being sold as-is and is subject to short sale approval.