Urban quality, real estate values and property taxation are different factors that participate in defining how a city is governed. Real estate values are largely determined by the characteristics of urban environments in which properties are located and, thus, by quality of the location. Beginning with these considerations, this paper explores the theme of urban quality through a study of property values that seeks to define all physical (and thus measurable) characteristics that participate in defining urban quality. For this purpose, a multiple linear regression model was developed for reading the residential real estate market in the city of Pescara (Italy). In addition to the intrinsic characteristics of a property (floor area, period of construction/renovation, level, building typology and presence of a garage), input also included extrinsic data represented by the Urban Quality Index. Scientific literature on this theme tells us that many independent variables influence real estate prices, although all are linked to a set of intrinsic characteristics (property-specific) and to a set of extrinsic characteristics (specific to the urban context in which the property is located) and, thus, to the quality of urban environments. The index developed was produced by the analytical and simultaneous reading of four macrosystems with the greatest impact on urban quality: environment, infrastructure, settlement and services (each with its own subsystems). The results obtained made it possible to redefine proportional ratios between various parts of the city of Pescara, based on a specific Urban Quality Index, and to recalculate market property values used to calculate taxes in an attempt to resolve the inequality that persists in this field.