Urban façade heterogeneity is not merely a product of architectural style or aesthetic preference, because façades emerge from interactions between social, economic, cultural, and institutional relations and urban context. This study interprets the social, economic, cultural, professional, and contextual factors associated with the physical heterogeneity of urban façades along Amir Kabir Corridor in Kashan. A qualitative case-study strategy was adopted. Data were collected through field surveys and photographic documentation of 10 selected façades, together with 20 semi-structured interviews with experts in architecture, urban design, urban planning, landscape architecture, and urban management. Cases were selected through purposive maximum-variation sampling, considering style, scale, materials, ornamentation, and contextual responsiveness. Interview data were examined through directed content analysis using a deductive–inductive approach. Physical analysis and expert perspectives showed that façade differences extend beyond formal choices and may be interpreted through owners’ and designers’ preferences, professional knowledge and attitudes, economic conditions, the construction market, urban regulations, and contextual characteristics. Four dominant patterns were identified: “display-oriented distinction,” “distinction accompanied by scalar dominance,” “context-responsive distinction,” and “contemporary expression.” Architectural distinction does not inherently generate heterogeneity; rather, discontinuity and reduced visual coherence become more likely when differences in form, materials, color, height, ornamentation, or skyline are coupled with weak relationships to the surrounding frontage. Bourdieu’s concepts of capital, taste, and distinction explained preferences and modes of social representation, while Lefebvre’s theory of the production of space situated these preferences within economic, institutional, and physical contexts. Because the owners, developers, and designers of the selected buildings were not interviewed, this relationship remains interpretive and does not establish a direct association between actors’ capital and façade characteristics. Accordingly, heterogeneity emerges when architectural distinction coincides with weak contextual relationships concerning scale, skyline, rhythm, materials, and proportions.