Outstanding craftsmanship and modern comfort come together in this exceptional Tallmadge & Watson Prairie School home. Built in 1915 and thoughtfully expanded over time, this property showcases timeless architecture, beautiful details, and a flexible layout filled with natural light-offering the perfect canvas to create a home that reflects your lifestyle and needs. Featuring unique art glass, a wood-burning fireplace, and finely crafted millwork, the formal living area opens to a sun-filled west-facing sunroom on one side and a cozy sitting area on the other. The formal dining room, highlighted by gorgeous French doors, flows into a spacious family room and adjacent kitchen, creating a sense of connection throughout the main living spaces. The family room, filled with light from windows on three sides, features a gas fireplace, a casual dining area, and a beverage bar. Open to the family room, the thoughtfully designed kitchen includes a center island, peninsula with seating, custom cabinetry, double ovens, a Viking range, and a Subzero refrigerator-blending beauty and function for everyday living and easy entertaining. A large main-floor office with two built-in desk areas, clever storage, a balcony, and a gas fireplace creates a versatile, comfortable workspace. Upstairs, five bedrooms and three full bathrooms offer generous, well-planned space for everyone. The primary suite feels like a true retreat, with custom closets, distinctive built-ins, a gas fireplace, and a spa-inspired en-suite bath featuring a jetted tub, dual vanity, and walk-in shower. The second and third bedrooms share a Jack-and-Jill style bath, while a tandem office offers even more flexibility. A full hall bath and upstairs laundry provide additional convenience. The lower level with high ceilings expands the living space even further with a second family room, a second full kitchen with additional laundry space, a full bathroom, fitness area, sauna, abundant storage, and bonus rooms ready for whatever inspires you. Wine cellar? Tasting room? Craft studio? The options are endless! Outside, the beautifully landscaped yard includes multiple patios, a deck, and lawn areas that offer a range of spaces for playtime, special gatherings, or simply relaxing together. Hard to find in Oak Park, this home includes an attached two-car garage with an electric car charger, plus a paver parking pad that can accommodate up to five cars. Additional highlights include a slate roof, flagstone walkway, three-zone HVAC system, 200-amp electrical service, updated plumbing, lower-level drain tiles, a new backyard fence, and an in-ground sprinkler system. Ideally located in a highly walkable neighborhood, this home is just blocks from the schools and downtown Oak Park, the Green Line train, and favorite local spots like Maya del Sol, Club Pilates, and Fairgrounds Coffee. Inspired design meets everyday comfort in this one-of-a-kind home!