Coworking space is an urban phenomenon, but it is interesting to explore their potential diffusion in non-core areas because of the positive direct and indirect effects that it can produce (direct effects on the coworkers and indirect effects on the urban environment and planning). This chapter aims to fill the gap in the literature on the effects of coworking spaces (CSs). By conducting an empirical study, the “indirect” effects of CSs on the urban context in Italy are explored, with a focus on pole and non-pole areas, as defined in Italy by the National Strategy for Inner Areas (Strategia Nazionale per le Aree Interne—SNAI). The empirical study is based on an online survey addressed to coworkers (CWs) of the 549 CSs located in Italy (as of January 2018): 326 CWs from 118 CSs have responded. The data are then elaborated by means of descriptive statistics and econometric analysis (propensity score matching/counterfactual). This geographical focus will allow us to understand whether and how CSs may be beneficial also to non-pole areas by promoting: entrepreneurial milieu; knowledge creation by retaining knowledge workers; and the creative class, social inclusion, and spatial regeneration. The findings suggest implications for policymakers and opens new avenues for further research.