The insights of Austrian philosopher Ludwig Wittgenstein can be useful in understanding the intricate dynamics of contemporary architecture and urban life and juxtaposing various facets of modernity and historical context. In his text, 20th-century modernism, which focuses on logic, modernity, technology, and spiritual matters, is intelligible. Wittgenstein was an analytic philosopher who believed in the correspondence between the real world, thought, and language. This study aims to analyze Wittgenstein's opinions and uses them to define a conceptual model that includes four components: Logic, avoidance of psychologism, viewing from the perspective of eternity, and modernity. The components are divided into ten subcomponents in architecture: Logic, usefulness, function, style, decorations, transcendence, positive feelings, tolerance, modernity, and technology. There was a focus on six cases, three historical buildings, and three contemporary ones in Semnan. Two questionnaires for citizens and experts have been prepared, and a field study has been implemented after the validity assessment. Then, the results of the questionnaires were entered into the data bank in IBM SPSS and were analyzed and compared. The findings show that three of the ten model variables, attention to excellence, creating a positive feeling, and a positive approach to technology, are ranked higher than the other variables, with an importance of nearly 80%. The acceptability of all three historical buildings is higher than the three contemporary buildings in both groups of citizens and experts, but the difference is much greater among experts.