Welcome to this timeless Greystone Two Flat, ideally situated in the prestigious Frank Lloyd Wright Historic District within the heart of Downtown Oak Park, where historic elegance meets modern opportunity. This exceptional property blends enduring architectural character with thoughtful updates, making it an outstanding opportunity for both owner-occupants and investors. The first floor unit has been tastefully refreshed with new interior paint all throughout, newer quartz countertops, stainless steel appliances, updated lighting, two spacious bedrooms, a beautifully appointed full bath, and a heated rear sunroom that serves as the perfect den retreat and/or an office/entertaining space. The second floor unit offers an equally inviting floor plan featuring two spacious bedrooms, a full bath, and an elegant front flex room that can be suited as a home office, library, sitting room, or additional living space and its heated rear sunroom creates yet another warm and versatile setting while preserving the home's original architectural charm. Every detail reflects pride of ownership. Additional highlights include newer windows throughout, hardwood floors throughout both units, separate utilities, an unfinished basement offering generous storage along with a washer and dryer for owner/tenant convenience and a beautifully reimagined front porch that welcomes relaxation, guests and seamless curb appeal. One of the property's most extraordinary features is its three private exterior parking spaces, located to side of the home, a true luxury in this coveted neighborhood and the only property on the block to offer dedicated parking. Whether envisioned as an owner-occupied investment, an elegant multigenerational residence, or a premier addition to a real estate portfolio, the possibilities are remarkable. Live in one residence while generating rental income from the other, or maximize returns with both units. The second-floor is occupied by a long-term tenant paying below market rent, presenting immediate value add potential. Both units offer the opportunity to command rental income approaching $2,400 per month, creating an attractive investment profile in one of Chicagoland's most sought after communities. Perfectly positioned in the vibrant heart of Downtown Oak Park, residents enjoy an irreplaceable location and walkable lifestyle surrounded by acclaimed restaurants, boutique shopping, artisan cafes, wellness studios, entertainment, neighborhood parks, and everyday conveniences. Proximity to Downtown Forest Park, the CTA Green Line, Metra, and an effortless commute to Downtown Chicago place the very best of the city and suburbs within easy reach. This is more than a two-flat. It is an opportunity to own an enduring piece of Oak Park's architectural legacy while embracing the lifestyle that one of Chicagoland's most desirable historic neighborhoods has to offer. Schedule your private showing today!