Dejima and Choryang Waegwan are resident areas established by the government to accommodate the Dutch and Japanese traders respectively who came for commercial trade activities. This was established to prevent the local citizens to communicate with the foreigners. Dejima and Choryang Waegwan have both similarities and differences on their purpose of establishment, which reflects the way of life and intercultural exchange of the foreigners. This is an empirical study that investigates the trade operations and way of life of the foreigners in the settlement areas on the Northeast Asian Sea Region cross-cultural network. Therefore, This paper analyzes the relationship between the trade operations and way of life in the settlement areas based on the establishment of schools, the expansion of surrounding facilities, and the spread of western studies. We also empirically analyzed the perception of each factor by setting up a model related to how it affected the foundation of modernization of both countries. A structural equation model was adopted to test the relationship between the factors described above. The summary of the study is as follows. First, settlement areas and the spread of western studies were found to have a significant effect in Dejima and Choryang Waegwan. Second, settlement areas and school establishment were found to have a significant effect in Dejima and Choryang Waegwan. Third, settlement areas and expansion of surrounding facilities were found to have a significant effect. Fourth, the dissemination of western studies and foundation of modernization had a significant effect in Dejima but not in Choryang Waegwan. Fifth, school establishment and the foundation of modernization had a significant effect in Dejima and Choryang Waegwan. Sixth, the expansion of the surrounding facilities and foundation of modernization did not show a significant effect in Dejima and Choryang Waegwan.