Early 20th century Singapore was faced with the problem of overcrowding. The attendant problems of a rapid increase in population density, namely the lack of proper housing and sanitation, resulted in the issue of an appropriate residential environment emerging as an important task in urban planning. It was necessary to construct housing estates in order to solve this issue. At that time, the British colonial government attempted to transplant modern technology into the construction process of a residential complex system. However, Singapore’s climate and traditional lifestyle made it impossible to apply the British modern system in a straightforward manner, and in the process, a number of transformations emerged. With a specific focus on the Tiong Bahru estate, one of Singapore’s representative public housing projects, from the 1930s through the 1950s, this study intends to look at the way in which such residential estates were assimilated into local surroundings, and the effect of the transplantation of British concepts of modern housing theory. Therefore, the study is divided into an examination of the estate both before and after the turning point of World War II. This study confirms that the difference between the pre-war and post-war planning strategies for the Tiong Bahru estate were made according to the concept of ‘open space.’