In 2014, a non-governmental organization called HOGAR SÍ initiated the Hábitat program as a pioneer attempt to implement the Housing First model in Spain. The present study is part of the evaluation of this program, which was carried out from May 2015 to February 2020 using a form of a randomized controlled trial. The treatment group was compared with a control group (people experiencing homelessness but not selected as Hábitat users), keeping track of their evolution over 18 months. Among the many dimensions that were evaluated (coverage of basic needs, life satisfaction, victimization, physical and mental health, etc.), the study analyzed social support and leisure activities involving the use of mobile media and other communication technologies—along similar lines to some previous research. The main results show that participating in the Hábitat program brought a few improvements in digital inclusion. That is the case of the higher use of mobile phones to receive calls, to connect to the Internet, or to have contact with relatives, partners, or friends. These gains seem to be significant for the increase in perception of available social support by Hábitat users, whereas these changes did not occur in the comparison group to the same extent. Additionally, participating in the program enhances satisfaction with leisure time, as well as the frequency of carrying out some activities such as shopping, watching TV, or doing a pastime or hobby. It could be concluded that the Hábitat program achieved significant improvements in areas beyond specific housing services. The positive effects regarding social support and leisure activities seem to be partly channeled through mobile phones and digital applications; nevertheless, we are aware that further research and discussion on the active role of these technologies in helping people experiencing homelessness is still necessary.