Set on a picturesque, tree-lined street in the sought-after Audubon School District, this beautifully appointed five-bedroom, 3.1-bath Roscoe Village residence delivers exceptional space, timeless character, and an effortless indoor-outdoor lifestyle. An elegant living room with a tray ceiling flows into the formal dining room, while rich hardwood floors, crown molding, custom millwork, and a striking iron-and-wood staircase add architectural distinction throughout. At the rear of the home, the expansive eat-in kitchen has been elevated with Taj Mahal quartzite countertops and backsplash, refinished maple cabinetry, updated hardware, stainless steel appliances, and a double-oven range. The kitchen opens seamlessly to an inviting family room anchored by a beautifully retiled fireplace, creating a sophisticated yet comfortable setting for everyday living and entertaining. French doors extend the space onto a large, sun-filled deck ideal for al fresco dining and relaxed summer gatherings. Three bedrooms occupy the upper level, including a serene primary retreat with soaring vaulted ceilings, skylights, a sleek linear gas fireplace, and a private balcony overlooking the backyard. The fully renovated primary bath offers a spa-like escape with a marble shower, soaking tub, heated porcelain tile floors, dual vanities, and refined lighting. Custom closet organizers, room-darkening shades, and refreshed flooring further enhance the home's comfort and functionality. The finished lower level provides exceptional flexibility with a spacious recreation room, two additional bedrooms, a full bath, and a convenient mudroom. Meticulously maintained and thoughtfully improved, the home also features updated patio doors, newer laundry appliances and water heater, an electric sump pump, recent masonry and tuckpointing, and updated HVAC systems. Complete with three fireplaces, multiple outdoor spaces, and a 2.5-car garage, this sophisticated residence offers gracious city living moments from the acclaimed dining, boutiques, and cafes along Roscoe Street, St. Benedict, the Paulina Brown Line, and near Hamlin Park.