Detached houses represent a significant part of Italy’s housing stock, built chiefly between the post-war period and the 1970s. Here defined as ‘family homes’ due to their role in life courses and the involvement of residents in their construction, they are today at the centre of transitional processes. Demographic and social changes, obsolescence, and shifts in housing preferences create a complex scenario. This contribution focuses on the family home in medium-sized towns, with particular attention to the Emilia context. Design explorations highlight the interrelations between the reform of public space and targeted interventions to upgrade housing, questioning how to continue to ‘live well’ in these settings.