In this research, tree sensitivity to the surrounding highly paved environment was analysed at several locations within one urban core (Novi Sad, Serbia). In the future, urban areas will become denser and will, in interaction with intensive climate change, negatively affect the urban forestry performance. Hence, in-depth understanding of the interactions between site-specific parameters, such as pavement and trees, is necessary. When conducting analyses, in this research the data was separated into four groups (0−2; 2−4; 4−6; >6 m) by two grouped parameters that define the interaction between trees and paved surfaces across the streets. The findings revealed that paved surroundings exerted the most significant effect on tree dimensions and lower on vitality. Moreover, tree height, diameter at breast height, crown width and phytopathological and entomological damage emerged as the most reliable indicators of plant stress caused by the negative influences of a paved environment. Reduced uniformity was noted for trees closer to the traffic and in areas with a narrow landscape strip. In general, the distance from the traffic has a stronger influence than the width of landscape strip on the analysed tree characteristics. Furthermore, the sycamore maple and its red leaf cultivar can be recommended for planting in highly paved areas across streets.