In this paper, the specificity of release and transformation processes of real estate markets in two postsocialist bloc countries, i.e. Bulgaria and Poland, was diagnosed. Comparative analysis of the conditions and directions of change was used as a tool to clarify the current situation, current status and characteristics of these markets. Comparison of Poland and Bulgaria also indicates the prospects for the development of real estate markets. The article is an attempt at assessing the condition and evolutionary progress of the residential segment. The authors also selected obstacles and factors promoting the development of real estate markets in the analyzed countries. This will either enable the critical assessment of changes observed in the past, or prove helpful in the context forecasting market phenomena.