The purpose of the present study was to investigate the relationship between perceived parenting style and life satisfaction among adolescents transitioning from middle to high schools and to ascertain whether self-esteem functions as a mediating variable between the two aforementioned variables. Based on the results of literature review, a research model, in which there were perceived parenting style, self-esteem, and life satisfaction as latent variables, was designed. The current study analyzed the 6th and 7th wave data of the 4th grade panel of elementary school from the Korea Children and Youth Panel Survey (KCYPS). Major results were as follows. First, perceived democratic parenting style had a significant positive effect on life satisfaction whereas controlling parenting style did not have a significant impact on life satisfaction. Second, self-esteem partially mediated the effect of perceived democratic parenting style on life satisfaction. Third, self-esteem fully mediated the effect of perceived controlling parenting style on life satisfaction. Finally, implications and recommendations were provided to improve parenting style and to enhance self-esteem of adolescents experiencing school transitions.