The role of the private rented sector (PRS) in housing has come to the forefront in the European housing policy debate in recent years, and was further underlined by the Great Financial Crisis and the burst of the housing (credit) bubble. The need to overcome the prevailing home ownership bias in nearly every European housing regime and to support intermediary housing tenure forms besides social housing has become clear in recent decades. Relatively little effort has been put into the study of housing regimes in Central and Eastern Europe (CEE), partly because of the lack of reliable statistical data. Privatization and marketization efforts in the region were vast, radically reducing the social housing sectors in CEE. Despite the clear need for rental housing, PRS remained residual. This chapter sets out to explore the micro-level actors and behaviours that cause the sector’s apparent stagnation, and the macro-level structural factors that explain these behaviours. Our goal is to explain the current state as well as the possible future role of PRS in CEE, but we believe that our findings also apply to the housing environments of other European countries where the expansion of PRS remained unsuccessful in recent years.