The main purpose of this study is to compare the differences in job satisfaction among public and private kindergarten school teachers in Cyprus. These comparisons take place from the perspectives of the teachers themselves and how they evaluate the working conditions in their own schools. More specifically, a series of three logistic regressions and a MANOVA were performed to predict whether the teachers are employed in private or public schools based on (a) the motivational factors that influenced them to enter the teaching profession, (b) their satisfaction with their working conditions, (c) the status and recognition that they receive, and (d) their satisfaction with the work of educational boards and associations. The results are interpreted in the context of how a country's cultural, social, and economic structures contribute to the development of particular forms of private/public schooling and the ways in which these structures seem to influence teacher job satisfaction.