This article engages signage as a medium through which urban stakeholders negotiate the politics of housing redevelopment and gentrification in cities. Focusing on Toronto, we examine housing-related signage in three neighbourhoods where social mix approaches to redevelopment have ushered in gentrification: Parkdale, Regent Park, and Moss Park. We identify three types of signs through which these politics are expressed: notice of proposed development boards, developer-branded placards, and paper posters. By analyzing both the original contents of and ad hoc changes made to select instances of these signs, we identify that gentrification through housing (re)development is contested, de- and re-politicized and resisted. In Parkdale, notice of proposed development boards communicate imminent transformations of the neighbourhood, while constituting a medium through which they are contested. In Regent Park, developer-branded placards depoliticize redevelopment through discursive commodifications of diversity, while also allowing for these commodifications to be repoliticized. In Moss Park, paper posters mobilize grassroots resistance to private condominium development. We argue that more attention should be paid to ad hoc alterations to signage beyond their explicit messaging, as a source of street-level insight into how multi-stakeholder gentrification politics materially unfold in cities.