Welcome to this meticulously crafted single-family home in the heart of Roscoe Village/Southport Corridor, where vintage charm meets modern luxury. Originally a classic brick two-flat, this unique home has been transformed into a spacious single-family residence with thoughtful updates throughout. The property offers easy living, just steps from public transportation, great restaurants, local bars, top-rated schools like Hamilton Elementary, the shops of Southport Corridor, and everything Roscoe Village has to offer. The main level features a perfect layout with a beautiful kitchen that includes quartz countertops, white cabinetry, and black hardware, plus an inviting sunroom off the kitchen-ideal for morning coffee. The main level is complete with a dedicated dining room adorned with accented wallpaper, a cozy living room with beautiful wainscoting and molding, custom roller shades, and a third bedroom currently utilized as an office, outfitted with custom built-ins and Gucci wallpaper. The full bathroom boasts a vintage clawfoot tub, upscale finishes, and California closet built-in storage. The bright, airy second floor showcases high ceilings, hardwood flooring, and a versatile floor plan with a second living space, complete with a kitchenette, cozy den, as well as a second bedroom. The primary bedroom includes a spacious walk-in closet and custom motorized shades, while the large bathroom is highlighted by penny tile floors and a walk-in shower. The lower level offers two additional bedrooms, a convenient office nook, and a luxurious full bathroom with West Elm finishes. This level also features an unfinished section with ample storage space and a laundry area. This home truly checks all the boxes, with a new stamped patio and walkway that lead to a beautifully landscaped backyard, perfect for entertaining, alongside a two-car brick garage.