The article deals. with the problem of difficult life circumstances of the middle class in Slovakia in 20th century. Comparing the atributes of groups and common values of two professional groups members (entrepreneurs and private vine-growers) in two different towns in Slovakia (Trencin and Modra) the authoresses tried to characterize and describe the main features of social transformation.The submitted study is an attempt to empirically examine the situation at the period of social and post-socialist transformation over the past 15 years. In the focus there are the re-establishment processes concerning small and middle entrepreneurs, namely private vine-growers, studied by a model analysis of both the examined groups and the situations in which they appeared after the nationalisation in 1948, and then after 1989. The main frameworks of the research are the value-systems of these craftsmen and vine-growers, changes of the local community, formation and stability of social strategies and perspectives, legislature and real life in entrepreneurial activities. The authors paid a special attention to the first attempts of individual subjects to start an independent (private) business after 1989, their primary philosophy, strategies and objectives, and a gradual re-evaluation and modification of the goals under the impact of a triad of closely intertwined components of the process: modernisation - transformation - globalisation. Asking questions about the position of the middle classes, namely the social groups of small and middle entrepreneurs and vine-growers in the social structure of the chosen towns, the composition of these groups, their position in the town community, or whether they at all form a social group with some common consciousness, strategies and goals, the authoresses have sought to comprehend their contemporary social and economic position. An analysis and comparison of group value systems cherished by these professional groups before 1948 and then after 1989 reveal dynamism of the relation between the value ideal (the proclamation) and everyday life values (the reality). From the methodological aspect, the study is an attempt to carry out a horizontal comparison - a comparison within a social space: the country, the society, urban environment and historical time are identical, what is different are these two different components of the middle classes at two different towns. Comparing the results of the research the authoresses came to conclusions that both the fates of the groups and the group values and their transformation (emerging from the strategies, goals and everyday behaviour of individual members of both examined groups) exhibit many common as well as different features.