In the built-up areas of large cities in Japan, urban renewal by individual rebuilding is progressing, and there is concern about the transformation of townscapes. In this study, we focused on the transition of cityscape rules and the actual situation of urban area renewal along the Midosuji avenue, and considered the formation process of urban landscape. As a result, along the Midosuji avenue, the building forms are controlled by the cityscape rules, and a new skyline with eaves heights of 50m is being formed. We grasped the trend that the wall materials of roadside buildings are standardized to stone and glass due to the intention of the designer. it was shown that how to create continuity of roadside buildings is an issue in future cityscape control.