Individual well-being is a multidimensional concept based on the physical and psychological dimensions. As far as psychological well-being is concerned, there are several factors affecting its value, including income, age, gender, education, civic status, and employment. One of the variables which have been considered in the literature is related to the place of residence, specifically urban or rural settings. The purpose of this population-based country study is to examine the association between subjective individual well-being and urban and rural areas in Italy, comparing the data of two survey waves (in 2008 and 2018) in a statistically significant sample of 1500 citizens among the Italian population. At a general level, results show a similar level of subjective well-being among rural and urban dwellers in 2018, while in 2008 the score for perceived well-being was higher in the rural context. The most interesting results, however, concern the variation of the determinants of well-being in the two areas, and the increasing relevance of the social and cultural aspects of rural and urban life.