This work presents an approach used to assess the quality of soundscape in urban spaces. It consists in analyzing and correlating psychometric tools that measure the perception of environmental quality and in correlating subjective acoustic data with objective investigation of acoustic parameters. Survey has considered selected key-spaces of two districts of Turin (Italy), during summer 2010, winter 2011 and winter 2012, subdivided in nodes, paths and edges. The main aim of the work was to differentiate between pleasant and unpleasant urban areas, using a criteria different from the one that is currently adopted by acoustic specialists and which has limited relevance on open space comfort. One of the main finding is that, among all the environmental aspects, only the pleasantness of the sound environment is positively correlated to the overall environmental quality. Two well separated clusters classify the key-spaces with respect to sound pleasantness. The first cluster, characterized by lower pleasantness, groups the key-spaces categorized as both edges and nodes, while the second cluster groups the paths. These two clusters have been confirmed by a discriminant analysis on the objective acoustical factors, determining that a lower intensity and a greater fluctuation lead to a greater sound pleasantness.