The Digital Grey Divide (DGD) is a phenomenon that refers to the digital inequality existing among the elderly in using digital tools. DGD could generate social exclusion and hinder elderly well-being because today many aspects of life are online. The objective of the research is to compare the urban and rural group to see if a digital divide is present and whether psychological and cognitive well-being can be predictors of usage. The research involved 100 elderly people (belonging to two different areas: one rural and one urban) aged 65 to 90 (M = 72.3; SD = 6.4) with intact cognitive functioning investigated by the MMSE test. A socio-anagraphic module to investigate digital use (DU), a questionnaire on cognitive reserve (CRIq), and a questionnaire investigating well-being (Ben-SSC) were administered. Results showed that the two groups differ in terms of access and use of digital tools (F = 28.34, p < 0.001), with the urban group reporting higher levels of access and use. Moreover, in the urban group, psychological well-being has an inverse relationship with digital, while in the rural group, the relationship between cognitive well-being and use is direct. Therefore, the study aims to highlight how even in developed countries there can be a digital divide (DD) given the risks of exclusion, particularly for the elderly population. For all these reasons, it is necessary to pursue interventions to achieve a higher level of digitalization and sustainable development among the population. Given the importance of this phenomenon, it is necessary to address the issue of DD in various spheres of life: political, social, economic and care.