A rare find in Helena's coveted Upper East neighborhood, this spacious brick 4-plex combines timeless character with smart investment potential. The property offers ground-level entry and plenty of off-street parking off the back alley, with room to build garages or additional storage, and the two units off Winne offer a 2-car parking pad! From the upper units, a shared interior stairwell leads downstairs to the mechanical room, storage lockers, and two washer/dryer sets designated for those units, while the two upstairs units each enjoy their own in-unit washer/dryer. Electric and gas separately metered, with tenants responsible for their own usage, and gas hot water heat runs through individual hot water heaters in each unit for added efficiency. The layout includes three spacious 2-bedroom/1-bath units and one 1-bedroom/1-bath unit, ideal for a mix of tenants or flexible owner-occupant living. Many windows have been replaced, with newer doors and flooring already in place in two of the units, and a new roof in 2022 via Perschon Roofing adds peace of mind for years to come. Out back, a beautiful yard with mature trees adds charm and curb appeal, offering a private & peaceful setting for residents to enjoy. Just minutes from the Capitol, St. Peter's Hospital, and the scenic South Hills trail system, this property offers the best of Helena living: walkable charm, outdoor access, and everyday convenience. With private entry, dedicated parking, and quality updates throughout, this is a standout opportunity for investors or an owner-occupant looking to put down roots in one of Helena's most desirable neighborhoods.