The Japanese architect Yoshikazu Uchida planned the estate plan of Osaka Hokko Co. Ltd. from 1920 to 1922. Through this study, we aim to clarify Uchida’s plan for outdoor spaces such as roads, parks, and plazas, and his ideology on them considering his estate plan. To achieve this purpose, we analyze letters sent mostly from the corporate insiders to Uchida, planning documents, and four drawings. The results show that Uchida used conflicting ideas depending on the location. For example, Cul-de-sacs were planned in residential areas to save road space, on the other hand, a wide road was planned with building setback to enhance the dignity of the estate. Furthermore, Uchida intended to provide parks and plazas to the residents from the perspectives of health and sanitation. Regarding the parks, Uchida assigned different functions to each park: for attracting visitors, for strolling, and for children to play. Additionally, Uchida suggested the plan of a wide road combined with boulevard trees and large buildings such as apartments. The circular plazas were also planned to be surrounded by buildings. The above-mentioned examples demonstrate how Uchida planned the outdoor spaces in relation to the buildings around them.