This article investigates three South African novels in an attempt to map the movement between transitional cultural production and post-transitional literature of the present. I briefly outline Phaswane Mpe’s Welcome to our Hillbrow (2001) as a formative text of the South African transitional period before discussing Kgebetli Moele’s Room 207 (2006) and Ceridwen Dovey’s Blood Kin (2007) as post-transitional texts. These novels all circle around issues of place and space, while also revealing the shifts in South African cultural history, as they comprise a set of related perspectives that inscribe meaning across times and spaces. I argue that a palimpsestic reading of this fiction opens up the possibility of reconceptualizing the relationship between space, place, and transnational connectivity. Each of the three texts under discussion writes the space of the city as a type of situated transnationalism where the local and the global exist as coeval discourses of signification. The fecundity of a palimpsestic reading lies in the revelation of how one transitional experience is already present in another. By inscribing one discursive act over another, the ruptures and continuities between textualizations reveal a wealth of imaginaries that, I argue, define the idea of post-transitional South African literature. But perhaps most importantly, the post-transitional can be read as a palimpsestic concept itself, much like the fiction explored in this article, in that it enables a reading of the new in a way in which the layers of the past are still reflected through it. Rather than moving in a temporal linear fashion, post-transitional literature creates a palimpsest in which we can read the imaginaries circulating through and shaping South African cultural formations today.