The TERSICORE project develops innovative models and protocols to investigate the psycho-social dimensions of urban regeneration. Central to the project is CitySense, a web-based application designed to capture users' experiences and interactions within regenerated urban spaces. The tool supports both the design phase, by exploring users' needs, expectations, social practices, and relationships with place, and the evaluation phase, by assessing satisfaction, perceptual changes, and patterns of use after interventions. The project proposes a methodological framework for cultural urban planners and digital designers to create participatory digital tools that enhance regeneration processes. This framework emphasizes key psycho-environmental factors, including place attachment, memory, emotional involvement, and perceived restorativeness, as drivers of meaningful engagement with urban environments. The methodology was tested through guided urban walks involving around 30 participants, combining pre- and post-walk questionnaires with in-situ digital interaction and focus groups after every walk. Results provide insights into how digital tools can foster engagement, support co-creation, and contribute to more walkable, inclusive, and people-centered urban regeneration strategies.