Fantastic opportunity to own an architectural gem in the Historic Winslow District of Shaker Heights! Perfectly positioned just steps from the vibrant Van Aken District, this two-family home offers an ideal blend of historic character, modern updates, and investment potential. Enjoy a walkable lifestyle home to local artisans, eateries, boutiques, and year-round community events that make this neighborhood truly special. The property offers incredible flexibility - ideal for an owner-occupant (the upper unit will be vacant upon transfer) or an investor ready to start earning on the occupied lower unit with the option to fill the remaining space. The lower unit features 2 bedrooms, 1 bath with a tiled walk-in shower, central air, and a private back deck. The upper unit boasts 4 spacious bedrooms, 2 full baths, front and rear porches, and two mini-split A/C systems for added comfort. Both kitchens feature modern finishes and stainless steel appliances, with dedicated laundry for each unit in the basement. A two-car garage and backyard fire pit add convenience and outdoor enjoyment. Major systems have been thoughtfully maintained and updated in recent years, including a boiler replacement for the upper unit (2025), a full lateral sewer line replacement (2025), newer hot water heaters (2022), lower unit furnace and A/C (2022). Come experience the charm and versatility of this turn-key historic home for yourself!