The essay addresses contemporary issues of living in intermediate mountain areas, focusing the emblematic case-study of Valtellina. Here, more than anywhere else, the effects of marginalization, abandonment, and fragility are condensed. Exactly because of this critical condition, it is possible to establish an interpretative process that, drawing on modern architectural culture foundations and principles, bases a renewed sense of living on the reuse and valorization of traces. The article shares an innovative approach to research, always with the aim of a transformative project which operates across scales and integrates skills and disciplines, proposing necessary readings and perspectives. With the awareness that these places are the main challenge of future habitability.