Rare investment opportunity in one of Livingston's most sought-after locations on South 9th Street. Situated on a spacious 0.321-acre lot-spanning four city lots-this unique property offers two homes and two 2-car garages, creating exceptional flexibility and strong income potential. Just one block from Water Works Park and two blocks from the Yellowstone River, with easy access to scenic walking paths leading to Sacajawea Park and the beloved Livingston Farmers Market, the location alone makes this a standout for both long-term and short-term rental appeal. The main residence blends historic character with thoughtful updates, featuring hardwood floors, 4 bedrooms, and 2 bathrooms. The open-concept living, dining, and kitchen area is filled with natural light from large windows that capture stunning views of the Absaroka-Beartooth Mountains. Recent improvements preserve the home's vintage charm while adding modern comfort-marmoleum flooring, antique fixtures, a cozy wood stove, newer stainless steel appliances, and an updated kitchen that stays true to the home's original style. The walkout basement expands the living space with 2 additional bedrooms, 1 bathroom, a laundry room, and a versatile flex space. A covered outdoor deck extends the living space, offering a perfect setting for relaxing or entertaining while enjoying the peaceful surroundings. An additional loft area upstairs-accessed by pull-down stairs in the hallway-provides bonus space ideal for storage, a studio, or creative use. Tucked behind, the charming cottage offers 1 bedroom and 1 bathroom with a full kitchen, featuring warm wood floors, marmoleum kitchen flooring, charming arched doorways, and a large picture window that fills the space with light-ideal for rental income, guest quarters, or multi-generational living. The oversized yard, framed by mature trees along quiet Cambridge Street, provides exceptional privacy-an uncommon find for an in-town property of this size. Currently occupied by terrific long-term renters, this property presents an immediate income-producing opportunity with upside potential in a premier Livingston location.