5900 Oak Street Classic 2-story home in the heart of Brookside offering a blend of original character and thoughtful updates. New roof being installed prior to closing, along with a new retaining wall and drainage improvements, providing added value and addressing major exterior improvements before move-in. The main level features spacious living and dining rooms, an updated kitchen with stainless steel appliances, breakfast area, and abundant natural light. Upstairs you'll find a generously oversized primary bedroom and a full bath, while the finished lower level adds a recreation room, second full bath, laundry, and additional storage for flexible living space. The built-in one-car garage provides convenient off-street parking. Recent improvements include a 200-amp electrical service upgrade, HVAC updates, replacement gutters with transferable warranty, and the new roof. Enjoy covered side and rear porches overlooking the yard, mature trees, and a location convenient to Brookside shops, Crestwood Shops, dining, parks, the Brookside Farmers Market, UMKC, the Country Club Plaza, and major commuter routes. Approximately 1 mile to the KC Streetcar via the Trolley Track Trail, providing convenient access to downtown Kansas City. This property combines historic architecture with functional living spaces, substantial exterior improvements, and documented mechanical updates, making it an excellent opportunity in one of Kansas City's established neighborhoods.