Classic Chicago two-flat in the heart of Andersonville, thoughtfully updated in 2025 to blend modern amenities with timeless vintage charm. An exceptional investment opportunity, this property is ideal as a live-in owner-occupied home with rental income or as a fully leased income-producing asset. The second-floor two-bedroom apartment features central A/C, in-unit laundry, and a beautifully renovated kitchen that opens to the enclosed back porch, creating space for both a large island and dining table overlooking the backyard. A formal dining room has been preserved, while the spacious living room and office nook open to a front porch overlooking the picturesque tree-lined street. The first-floor duplex-down offers five bedrooms (two on the main level and three below), providing exceptional flexibility for a growing household, guests, or home offices. The historic floor plan has been thoughtfully maintained on the first floor, featuring a formal dining room with the original built-in cabinetry and an enclosed back porch that serves as an ideal breakfast room or mudroom. The home includes three bathrooms including a beautifully renovated vintage-style bath on the main level, a spa-inspired ensuite and a second sophisticated lower-level bath. The finished lower level also offers a family room and in-unit laundry. Enjoy an evening on the porch, grilling on the back patio (with a gas hook-up), playing in the spacious turf backyard, or gardening. A two-car garage, newly re-sided in 2025, completes this exceptional Andersonville property.