The southeastern United States has undergone anthropogenic changes in landscape structure, with the potential to increase (e.g., urbanization) and decrease (e.g., reservoir construction) stream flashiness and flooding. Assessment of the outcome of such change can provide insight into the efficacy of current strategies and policies to manage water resources. We (1) examined trends in precipitation, floods, and stream flashiness and (2) assessed the relative influence of land cover and flow-regulating features (e.g., best management practices and artificial water bodies) on stream flashiness from 1991 to 2013. We found mean annual precipitation decreased, which coincided with decreasing trends in floods. In contrast, stream flashiness, overall, showed an increasing trend during the period of study. However, upon closer examination, 20 watersheds showed stable stream flashiness, whereas 5 increased and 6 decreased in flashiness. Urban watersheds were among those that increased or decreased in flashiness. Watersheds that increased in stream flashiness gained more urban cover, lost more forested cover and had fewer best management practices installed than urban watersheds that decreased in stream flashiness. We found best management practices are more effective than artificial water bodies in regulating flashy floods. Flashiness index is a valuable and straightforward metric to characterize changes in streamflow and help to assess the efficacy of management interventions.