Mass housing neighbourhoods (MHN) represent the leading pattern of urban transformation and expansion in the second half of the 20th century, and accordingly evaluation, regeneration and redesign of the MHN represent a necessary and challenging task in the contemporary research context. In the practical scope of MHN rehabilitation, various holistic approaches and design strategies are identified that affirm both ecological transition and social transformation of these urban settings. However, the level of application of such approaches across Europe varies greatly, and requires research initiatives of a comparative nature that open a cross-geographical debate at the European level. Although there is a series of evidence-based studies that define the conceptual framework of MHN, i.e., large-scale housing settlements, through historical-interpretative and chronological analyses, the academic debate on practical and feasible MHN rehabilitation and their sustainable integration into the urban development of cities at European level is underdeveloped. The specific objective of this paper is to establish preliminary insights into the current level of MHN rehabilitation and to identify challenges for further actions through (1) a comparative analysis of MHN role models from the second half of 20th century, and through (2) insights from an implemented expert questionnaire. The research engages a comparative case study analysis as the primary method and analyses MHN in Germany (as a representative of Western Europe) and in the two ex-Yugoslav countries, North Macedonia and Serbia (as representatives of Eastern Europe). This research has highlighted the main obstacles and challenges for MHN rehabilitation and demonstrated the importance of a multiscale approach to MHN analysis, having in mind that through the distribution of design values at the analysed spatial levels (neighbourhood level, building level, and apartment level) the application of affirmative indicators within different design values group is recognised.