Climate change-related impacts such as heat stress, extreme weather events, and their consequences are particularly felt within densely built-up urban areas. Urban re-naturalisation is recognised as a promising cost-effective strategy for improving urban resilience to these environmental and societal issues. In this respect, the present contribution focuses on a comprehensive city-wide assessment of street-level urban tree canopy to detect the existing vegetation gaps and identify re-naturalisation potentials within the urban fabric for the three largest cities in Austria (Vienna, Graz, and Linz). The study relies on QGIS and R software environments to carry out spatial data analytics on georeferenced tree cadastre data and the global map of Local Climate Zones (LCZ) to compute spatial density maps and urban structure parameters. The results suggest a rather random distribution of tree clusters and highly fragmented instances within the city. This fragmentation is predominantly observed within central densely built urban fabric for all three cities, with the absence of street trees in peripheral urbanised areas being more prominent in Graz and Linz. The computed percentage of potentially disconnected areas in terms of the tree canopy for Vienna, Graz, and Linz amounts to 45%, 54%, and 37%, respectively. The analysis of urban structure revealed a homogeneous densely built-up character over central districts and a dominantly heterogeneous character across non-central and peripheral districts with a more openly built fabric (this heterogeneity is, generally more prominent in the case of Graz and Linz). In general, there are numerous opportunities for urban re-naturalisation, focusing on urban trees within such openly arranged buildings. Due to the evident physical constraints of the urban space within central districts, the consideration of building-level greening (e.g. green roofs, green facades) may be a better approach to urban re-naturalisation in these cases. Given the further constraints imposed by the abundance of historic buildings, such measures may not be feasible in every event. Hence, this calls for consideration of novel, innovative and emerging greening systems with the proposition of movable vertical green screens and vertical gardens.