Timeless Tudor-style duplex located on beautiful, tree-lined Winslow Rd in the heart of Shaker Heights Historic district. This well-maintained property has been owned & lovingly cared for by one family, offering exceptional character, solid mechanical updates, & spacious layouts ideal for an owner/occupant or investor. Both units feature gorgeous hardwood floors throughout, classic architectural details, & generous room sizes. Each unit includes 2 bedrooms, an eat-in kitchen, a formal dining room, and a large living room with a beautiful fireplace. One bedroom in each unit offers an enclosed porch overlooking the backyard & the 3-car garage, while the second bedroom in each unit enjoys its own charming porch as well. Major improvements completed in 2025 include a full sewer line replacement from the house to the street, a new boiler for the 2nd-floor unit, & new hot water tanks for both the 1st & 2nd floors. The 1st-floor boiler is only a few years older. The 2nd-floor dishwasher is brand new. The second-floor unit has seamless access to the expansive third floor, which adds two additional bedrooms, a full bath, & a living room perfect for extended living, or a teen suite. The basement provides separate washers & dryers for each unit, all of which stay with the home. A home warranty is included for added peace of mind. With its prime location, classic Tudor charm, strong mechanical updates, & flexible floor plan, this duplex is an outstanding opportunity, especially for buyers seeking to live in one unit and rent the other. A rare find in Shaker Heights!