The present work is aimed at assessing the change in time of flood risk as a consequence of landscape modifications. The town of San Donà di Piave (Italy) is taken as a representative case study because, as most parts of the North Italy floodplains, it was strongly urbanized and anthropized in the last several decades. As a proxy for flood risk, we use flood damage to residential buildings. The analysis is carried out at the local scale, accounting for changes to single buildings; GIS data such as high-resolution topography, technical maps, and aerial images taken over time are used to track how the landscape evolves over time, both in terms of urbanized areas and of hydraulically relevant structures (e.g., embankments). Flood hazard is determined using a physics-based, finite element hydrodynamic code that models in a coupled way the flood routing within the Piave River, the formation of levee failures, and the flooding of adjacent areas. The expected flood damage to residential buildings is estimated using an innovative method, recently proposed in the literature, which allows estimating how the damage evolves during a single flood event. The decade-scale change in the expected flood damage reveals the detrimental effect of urbanization, with flood risk growing at the pace of a fraction of urbanized areas. The within-event time evolution of the flood damage, i.e., how it progresses in the course of past or recent flood events, reflects changes in the hydrodynamic process of flooding. The general methodology used in the present work can be viewed as a promising technique to analyze the effects on the flood risk of past landscape evolution and, more importantly, a valuable tool toward an improved, well-informed, and sustainable land planning.