Climate and human activities impact the timing and quantity of streamflow and floods in different ways, with important implications for people and aquatic environments. Impacts of landscape changes on streamflow and floods are known, but few studies have explored the magnitude, duration and count of floods the landscape can influence. Understanding how floods are influenced by landscape structure provides insight into how, why and where floods have changed over time, and facilitates mapping the capacity of watersheds to regulate floods. In this study, I (1) compared nine flood-return periods of 31 watersheds across North Carolina and Virginia using long-term hydrologic records, (2) examined temporal trends in precipitation, stream flashiness, and the count, magnitude and duration of small and large floods for the same watersheds, and (3) developed a methodology to map the biophysical and technological capacity of eight urban watersheds to regulate floods. I found (1) floods with return periods ≤ 10 years can be managed by manipulating landscape structure, (2) precipitation and floods have decreased in the study watersheds while stream flashiness has increased between 1991 and 2013, (3) mapping both the biophysical and technological features of the landscape improved previous efforts of representing an urban landscape's capacity to regulate floods. My results can inform researchers and managers on the effect of anthropogenic change and management responses on floods, the efficacy of current strategies and policies to manage water resources, and the spatial distribution of a watershed's capacity to regulate flooding at a high spatial resolution.