As a reaction to the critical writings of urban sociologists regarding the quality of post-Second World War large housing estates (monotonous architectural design, cheap/poor quality building materials, high building density, minimum dwelling sizes, overcrowding, etc.), fewer problematic types of mass housing neighbourhoods started to emerge, first in Western European countries in the 1970s, and later in Eastern European countries after they abandoned the planned economy system of the communist era and adopted the market economy system. One of the major concerns often raised in this regard is that, due to a variety of negative aspects associated with post-WWII housing estates, these neighbourhoods may eventually end up as concentrations of low-income households, after the more affluent residents relocate to the more attractive, less problematic residential neighbourhoods. Such developments are, understandably, undesirable. This concern inherently assumes that the inhabitants of post-WWII housing estates are not satisfied with their housing and are, as a result, expected to move away, as soon as they can. This hypothesis presents the focus of discussion in this paper. We examine its validity with the help of the findings of a comparative study between post-WII large housing estates and post-socialist multifamily residential neighbourhoods that was conducted in Slovenia in 2021. Contrary to the hypothetical assumptions, our analyses of the research results reveal that the inhabitants of post-WWII large housing estates are (a) generally quite satisfied with their dwellings and residential neighbourhood and that (b) a large majority of them have no intention to move. Understanding people’s satisfaction with their housing circumstances requires a complex analysis of their attitudes that goes beyond surface-level observations and encompasses a broader range of psychological and social influences on housing choices, suggesting the need to incorporate these aspects into future research. The consideration of these aspects is essential in order to ensure the longer-term sustainability of post-WWII large housing estates.