Historic cities, rich in heritage values and evocative of collective memories and meanings, also constitute crucial living environments for urban residents. These cities increasingly face challenges from urbanization and globalization, leading to cultural discontinuities and the homogenization of cityscapes. Such developments can diminish residents’ sense of belonging and identification with their cities. Emphasizing local residents’ satisfaction is thus essential to urban conservation. This study, using data from Dandong, China, employs Gradient Boosting Decision Trees (GBDT) to identify factors affecting residents’ satisfaction in historic built environments. The analysis reveals that over half of the variability in satisfaction is linked to distinct features of the historic environment. Among the fourteen key influencers identified, contextual order emerges as the most impactful factor, notable for its significant effects and interactions with other variables. This study also uncovers pronounced non-linear effects and thresholds for physically measured characteristics. For instance, open space markedly boosts satisfaction when exceeding 34%, satisfaction diminishes with travel times to heritage sites longer than 6.7 min, and satisfaction decreases when the entropy index for diversity surpasses 0.758. These findings provide critical insights for guiding urban conservation strategies and promoting a data-driven approach to enhance residents’ satisfaction in historic urban settings.