The hydrological functioning of urban trees can reduce stormwater runoff, mitigate the risk of flood, and improve water quality in developed areas. Tree canopies intercept rainfall and return water to the atmosphere through transpiration, while roots increase infiltration and storage in the soil. Despite this, the amount of stormwater that trees remove through these functions in urban settings is not well characterized, limiting the use of urban forests as practical stormwater management strategies. To address this gap, we use ecohydrological approaches to assess the transpiration rates of urban trees in different management settings. Our research questions are: Do transpiration rates of trees of the same species vary among different management contexts? Do relationships between environmental drivers and transpiration change among management contexts? These management settings included single trees over turfgrass and a cluster of trees over turfgrass in Montgomery County, MD, and closed canopy forest with a leaf litter layer in Baltimore, MD. We used sap flux sensors installed in 18 mature red maple (Acer rubrum L.) trees to characterize transpiration rates during the growing season. We also measured soil volumetric water content, air temperature, relative humidity, and precipitation at each site. In agreement with our initial hypothesis, we found that single trees had nearly three times the daily sum of sap flux density (JS) of closed canopy trees. When averaged over the entire measurement period, JS was approximately 260, 195, and 91 g H2O cm−2 day−1 for single trees, cluster trees and closed canopy trees, respectively. Additionally, single trees were more responsive to VPD than closed canopy and cluster trees. These results provide a better understanding of the influence of management context on urban tree transpiration and can help to identify targets to better manage urban forest settings to reduce urban stormwater runoff.