This chapter presents an evidence-based approach to mapping citizens’ affective and cognitive relationships with urban heritage sites in the city of Mykolaiv, Ukraine, during wartime. The study explores people’s evaluation of psychological features of seven centrally located sites selected for their potential relevance in urban regeneration initiatives. Using static visual stimuli, participants remotely evaluated the sites in terms of Emotional Response, Perceived Restoration, and Place Attachment. The analysis revealed consistently positive evaluations across all sites, with differences primarily in intensity rather than the specific type of emotional response (which mostly fell within the domain of high-arousal, positively valanced reactions such as excitement). The findings underscore the importance of integrating citizens’ experiential perspectives into urban regeneration processes, especially in conditions of uncertainty and fragility. The method offers a flexible, scientifically grounded framework for supporting inclusive urban transformations through the spatial representation of subjective data and the detection of patterns of collective perception, thus supporting design solutions grounded in a people-centered perspective.