Every summer, wildfires affect thousands of steep watersheds in Italy, causing the partial or complete destruction of vegetation, and changes in soil hydraulic properties. Such effects alter the hydrologic response of watersheds, increasing post-fire debris and sediment-laden flow hazard. This study characterizes the most relevant predisposing and triggering factors for a sequence of four post-fire flooding events, which, in the late summer-autumn of 2017, affected Montoro village in southern Italy. This research work consists of a fire severity assessment based on multispectral satellite images, characterization of meteorological systems and related flood-triggering rainfall, and provides an overview of the damage that occurred in the repeatedly affected urban area using crowdsourced data. The research findings demonstrate that the analyzed area burned with moderate-high (64.4%) and low severity (35.6%) levels. All the flooding events were triggered by rainfall evaluated as non-extreme, but with relevant peak intensities (I10 and I30), associated with the first convective storms impacting the burned watersheds. The crowdsourced data highlight the fact that roads and buildings on footslopes were inundated by mud and debris transported by rapid flows. The study identifies a clear relationship between wildfires and flooding processes and provides useful information for hazard assessment and emergency management operations.