Since 1895, the colonial Japanese rule of Taiwan had brought social and cultural impacts on all walks of life; painters were no exception. The traditional paintings in architecture have their root in Chinese calligraphy and paintings. However, during times of changes, new visual culture also comes into play. Traditional and modern styles of paintings co-exist in a residential space, creating a novel way of artistic representation. This particular phenomenon, born out of the distinct social and historical environments not only reflects the social background and trends of fashion, but also reveals the taste of common people. In this article, I study the paintings in residential buildings during 1920 to 1930, using both field research and related documents. I analyze the theme and content of paintings of this period through the background of painting craftsmen and elements of the mainstream art development. The objectives of my research include, (1) to investigate how such modern themes and content of residential house paintings relate to the social background; (2) to document life stories and professional experiences of these painters; (3) to conduct a comprehensive analysis of the relationship between the inception of modern images and the painters. I conclude that the arrival of trendy modern images indicates that politics and economic development of the society, as well as the mainstream arts style did have a significant impact on the traditional architectural paintings. Yet, individual artist's influence relates more to his own experience of apprenticeship. This study unveils new aspects of traditional architectural paintings during the Japanese Colonial Period. The conclusion helps us understand the influence of social environments on traditional architectural paintings and their artistic value.