Housing is one of the basic and most complex human goods. It is defined by many characteristics that determine the quality of living. In this research project, we treat housing as a good with physical and substantive characteristics, which are important indicators of its useful value or key indicators for measuring any changes in residents’ social values, which are reflected in their comprehension, perception, and needs regarding quality of living. In doing so, we focus on living in housing estates that were built under the socialist political and economic system and the subsequent transition to a market economy system (the post-socialist period). We proceed from the hypothesis that the changed social circumstances that characterize the post-socialist period have brought the residents new expectations regarding quality of living, which (may) consequently mean that housing estates from the socialist period have become less attractive to live in, because the residents have higher expectations or demands for a better housing standard and better quality of the residential environment due to changed values with regard to quality of living in housing estates. The study is designed to be comparative, because we are testing the hypothesis in two countries, Slovenia and Croatia, which share the same foundation for the emergence of the large housing estates built during the socialist period. Both were constituent parts of socialist Yugoslavia. Like in other socialist countries of central and eastern Europe, the construction of these housing estates continued in Yugoslavia until the late 1980s. It ended only after the collapse of Yugoslavia and the introduction of a new sociopolitical and economic system, when new typologies of collective housing construction began to emerge. Housing estates of the post-socialist period usually include smaller individual residential buildings, with a smaller number of apartments and a lower number of residents. This primarily applies to Slovenia, whereas in Croatia the construction of high-density housing estates continued during the post-socialist period, which means that housing construction differences began to emerge between the two countries during the post-socialist period. However, despite these changes and differences, the large socialist-era housing estates in both countries still represent an important type of the housing environment, or a significant proportion of the total housing stock, which we assume (given the hypothesis) to be inadequate for quality living due to obsolescence and changed values, and which needs thorough regeneration. Nevertheless, neither of these countries has adopted a national strategy for regenerating large housing estates, or guidelines to ensure a better quality of the housing and living environment. This research project’s ultimate goal, therefore, is to define—from the quality of living perspective—guidelines and recommendations for the appropriate regeneration of housing estates from the socialist period and the design of new housing estates that can be used in both Slovenia and Croatia. The basis for formulating proposals for preparing both national strategies will be the set of similarities and differences in perceptions and comprehension of the quality of living among housing estate residents, and their needs stemming from the new lifestyle values. From this perspective the research will be original, and the guidelines developed will be relevant to other central and eastern European post-socialist countries, especially those that were once part of Yugoslavia. This research is also of particular importance methodologically, because participatory data collection methods will be used: participatory action research, user-led research, and open democratic forum. It is precisely the lack of public participation in defining problems and solutions that has been a frequent (and frequently criticized) problem in post-socialist countries.