The process of dike-break flood propagation in typical urban street is highly complex. The presence of buildings and trees groups in urban street profoundly alters the flood dynamics, impacting the drainage capacity of the area. In this study, a generalized sink model representing a typical urban street was established, including trees groups, buildings, sidewalks, and stormwater drainage systems. The study measured the fluctuation of water levels within the street block and the pressure variation in the pressurized stormwater drainage network during the dike-break flood propagation. Furthermore, it conducted a comparative analysis to assess the influence of different arrangements of trees groups on the maximum water depth in buildings and the discharge capacity of the pressurized stormwater drainage network. Dike-break floods give rise to large-scale water leaps and the formation of thin layer water sheets near the buildings under the influence of buildings, water tank sidewalls, and tree groups. The water leap zones exhibit lateral migration and superposition on the sidewalks during the flood propagation, gradually dissipating and disappearing in the longitudinal direction of the street. In the presence of tree groups, the water levels significantly decrease in buildings and downstream street, while the discharge capacity of the pressurized stormwater drainage network shows a slight improvement as the road’s flood-carrying capacity increases. The pressure in the main pipes fluctuates due to the switching of the grate inlet drainage mode and the hydraulic transition process in the branch pipes. The research findings not only provide valuable validation data for numerical simulations but also offer theoretical guidance for urban flood management and landscape design.