The ‘family house’ has played a major role within the urbanisation processes that have been transforming the Italian landscape since the 1960s. It is a common feature of the widespread settlements that are part of what has been labelled the ‘diffuse city’ and was the subject of numerous studies during the 1990s. More than 20 years later, this paper returns to the topic of the Italian family house using a renewed methodological approach to describe relevant changes. The hypothesis here is that in order to grasp the tensions affecting ‘family houses’ in today’s context of demographic transition and increased imbalances between dynamic and declining areas, and to contemplate their future, the qualitative gaze adopted by scholars in the 1990s must be integrated with other investigative tools, focusing on demographic change, uses, and the property values of buildings. Using this perspective, the paper provides a series of ‘portraits’ rooted in four meaningful territorial contexts, portraits which may help scholars to redefine their imagery associated with family house and be useful for dedicated building policies.