The adoption of green roofs is an effective practice for mitigating environmental issues in urban areas caused by extreme weather conditions. However, certain design aspects of green roofs, such as the characterization of the physical properties of their substrates, need a better understanding. This study proposes a simple method for estimating two hydraulic properties of green roof substrates based on the evolution of moisture during drying periods, or drydowns, where evaporative processes dominate: the weighted-mean diffusivity and the saturated hydraulic conductivity. Soil moisture was monitored using 12 in situ sensors from 2015 to 2020 in a study involving six different green roof plots composed of various mixtures of demolition-recycled aggregates and organic substrates. A universal parameterization for determining water diffusivity in soils was applied to estimate the weighted-mean hydraulic diffusivity. As a by-product, the saturated hydraulic conductivity was estimated from the evaluated diffusivity and the measured water retention data. The median values obtained for and range from 14.5 to 29.9 cm2d−1 and from 22 to 361 cmd−1, respectively. These values fall within the ranges reported by other research groups using direct measurement methods and supports the validity of Brutsaert’s model for green roof substrates. Furthermore, an increase in and a decrease in were observed as the percentage of recycled aggregates in the substrates increased, which could be considered for design purposes.