The variety of post-socialist agricultural transitions in four different rural regions located in South Bohemia (Czech Republic), with respect to the utilisation of the older premises, is subject to analysis in this article. A complete database was constructed, containing the identification of agricultural premises in 1989 and their use in 2004 and 2017. From 1989 to 2004, a number of agricultural brownfields emerged, and many sites had been utilised for non-agricultural purposes. After 2004, the acreage of agricultural brownfields was reduced and new land-use utilisation for housing and, especially other non-agricultural activities, significantly increased. The transition in the utilisation of pre-1989 agricultural premises is strongly influenced by the social and economic contexts in which particular sites are located. Proximity to an upper-level regional centre is of crucial importance for decisions with respect to how (and if) the site will be reused. The peripheral location of the site also affects the level and the selection of options for the ways in which particular pre-1989 agricultural premises are used. In the case studies reported here, the marginality of particular regions is increased by their location in the border regions of outer peripheries, where the probability of the presence of agricultural brownfields and the probability of long-term abandonment of agricultural premises is higher. For the traditional developed countryside, we found a typical low level of the share of long-term agricultural brownfields. After 2004, the re-use of pre-1989 agricultural brownfields for agriculture was ascertained, which is complemented by their use for housing.