<p>This study presents a context-specific evaluation framework for assessing the landscape quality of Danjie Road in Loutang Ancient Town, Shanghai. Drawing on historical research, field surveys, expert consultation, and public participation, this study develops a seven-criteria, twenty-six-indicator system that integrates physical attributes with intangible dimensions such as memory continuity, cultural identity, and microclimate adaptation. Although the AHP–Entropy method is employed to balance subjective and objective weights, the core contribution lies in reframing the evaluation of heritage streetscapes as a multidimensional and culturally embedded process. The results indicate that historical and cultural values, along with aesthetic visual quality, are most critical to the perception of Danjie Road, whereas environmental performance and maintenance management remain underappreciated. The findings provide theoretical insights and practical guidance for the revitalisation of historic street environments and offer a transferable model for the integrated assessment of cultural landscape heritage.</p>