This is a research-based urban design project that explores how a landscape approach could contribute to regenerating a decrepit residential district. The focus is on a post-war housing area in Rotterdam, the Netherlands, called Groot-IJsselmonde. This site is a typical example of a post-war district in the Netherlands, with a layout clearly defined by plenty of green; good infrastructure; and a clear division among living, working, and recreation spaces. This research defines how this restructuring effort has been applied to the post-war neighborhoods in this district and what landscape architecture can contribute to this community’s sustainability. In order to better understand how the design of open spaces can improve community sustainability, this research ponders the following questions: What are the meaning and characteristics of restructuring post-war neighborhoods in the present day? What are the strategies for restructuring these neighborhoods? And what is the new role of landscapes in contemporary cities, especially in post-war neighborhoods? Also, as it is understood that a spatial program is the engine of a project and that urban agriculture has potential as a restructuring tool, in this study “productive landscapes” are employed as a major concept in the design and operationalized in a physical setting. In the end, this research proposes adding a productive function to any unused green areas and meaningless landscapes to help enhance both the economic and social elements of the community. As it is situated in a similar social context to this Dutch case (such as having entered a post-industrial society and regarding apartments as the major housing system), this study is expected to provide useful and practical lessons for current urban regeneration in Korea.