Urbanization in flood-prone areas is a critical issue worldwide. The historical floods, the urban expansion in terms of building footprint, the extent and construction period of inundated buildings with reference to two representative floods (5–6 November 1994 and 24–25 November 2016), and the ground effects and dynamics of these events were investigated in the cities of Garessio, Ceva, and Clavesana, along the Tanaro River (NW Italy). An integrated approach based on historical data analysis, photograph interpretation, field surveys, and GIS investigations was adopted, and novel metrics for quantitative analysis of urbanization and flood exposure at the individual-building scale were introduced. The considered cities were hit by damaging floods several times over the last centuries and experienced an increase in built-up surface after the mid-19th century, especially between the 1930s and 1994. The 1994 and 2016 high-magnitude floods highlighted that urban expansion largely occurred in flood-prone areas, and anthropogenic structures conditioned flood propagation. One of the rare Italian cases of the relocation of elements exposed to floods is documented. This research aims to emphasize the relevance of information on past floods and urbanization processes for land planning and land management and the need for land use planning for flood control to forbid new urban expansion in potentially floodable areas. The outcomes represent an essential knowledge base to define effective and sustainable management measures to mitigate hydrogeomorphic risk.