The ongoing digital transition profoundly affects people’s habits and customs, their lifestyles and also the choice related to the place to live. The choice related to the place to live is strongly conditioned by the incidence of the cost of housing (buying or renting), which is dependent on the market and income capacity. It should be noted, however, that the growing interest in the concept of well-being understood as a paradigm of quality of life may lead to new interests in residential demand effectively untying the digital transition - at least potentially - workers in the tertiary sector from the physical place of work. Based on the above, this paper aims to illustrate some results of a Project of Significant National Interest under the Ministry of Universities and Research (MUR)’s approved call No. 1409 of 14-9-2022 (PRIN 2022 PNRR) entitled “Housing mobility and digital transition. Evaluation tools and technologies for understanding current and future people’s living needs, supporting territorial governance and regeneration processes.” This Research project is configured as a prodromal study and investigation activity for understanding, among demographic phenomena, housing mobility, which significantly affects urbanization phenomena on which land use and protection, urban regeneration, and the protection and enhancement of agricultural activity, issues of interest to the PNRR, depend. In detail, the present work returns the results of a survey, conducted through the tool of the questionnaire, widely used in social research, aimed at investigating, with reference to the Tuscan regional territory, the subjective dimension in settlement choices, in order to identify the territorial areas that, without considering the market and objective qualification characters and therefore without objective feedback, are nevertheless more attractive.