This study examines the architectural heritage of Vlasotince, a small town in southern Serbia affected by long-term depopulation, economic stagnation, and insufficient institutional mechanisms for heritage care. The research provides a comprehensive and systematically documented basis for protecting the historic urban core—Stara čaršija—using an integrated methodology that combines archival analysis, urban and architectural surveying, interviews, and extensive 3D photogrammetric documentation. The collected dataset enabled the evaluation of cultural, architectural, and urban values, the identification of a coherent spatial cultural-historical unit, and the development of a typology of degradation affecting the historic fabric. Results show that 52% of buildings within the core possess exceptional or notable value, yet degradation is widespread: 40% of buildings exhibit altered openings or portals, 29% have lost decorative plasterwork, and 23% represent new constructions incompatible with the ambient character. Mapping values and vulnerabilities at the building level allow for the definition of priority interventions. The study demonstrates that combining digital documentation, spatial analysis, and value-based assessment offers an effective framework for heritage management in small towns with limited resources. The proposed methodological model is replicable and contributes to data-driven conservation planning, supporting the sustainable revitalization of historic urban landscapes in similar regional contexts.