Redesigning urban space has become integral to urban planning as a means of dealing with urban restructuring. It is about functional and spatial aspects. But also, it is about introducing new meanings into urban space when former meaning has become obsolete. In this article, the disappearance of retail shops from urban centres forms the impetus to a search for new meanings and designs of urban space. A transformation of obsolete urban centres into residential usage is considered. Three traditional urban elements are suggested as metaphors for a new hermeneutics of urban restructuring: the British PRECINCT, the Netherlandish STOEP, and the Greek AGORA. These elements are presented in their respective historical contexts, and their use in the present context of urban restructuring is considered as a remedy for transforming former vibrant shopping streets into residential districts. While the precinct and the stoep are still meaningful design concepts, the agora invites supplementary considerations due to the proliferation of ways people meet in urban space.