Families and schools are traditionally seen as substantial socialization agents forming adolescents' social values and their views of society. Special attention is paid to the question whether the relative importance of these influences remains stable in times of major social changes. In this study, two different generations of Czech middle adolescents are compared: (a) the "post-totalitarian" generation that grew up in the last decade of the communist regime and entered adolescence during the time of rapid political and socioeconomic changes (data collected in 1995) and (b) the current generation without personal experience with the communist regime, raised in a stable democratic society (data collected in 2010). Both groups of participants (total N = 2,127, aged from 14 to 17 years) were administered an identical questionnaire. First, we examined the changes in adolescents' perception and evaluation of the society over the last 15 years. Today's adolescents perceive society more as a community and their future orientations are more focused on materialistic and less on environmental values. While the emotional relationship between the children and parents remains the same, adolescents learn a somewhat different message in the family, emphasizing self-reliance. School environment is perceived more as positive and engaging than 15 years ago. Second, we predicted adolescents' social views and values from their assessment of family and school environment. Our results show that the effect of parental values on adolescents' value orientations is higher in the current generation. Positive school environment contributes to the development of socially responsible orientations despite the changes in society.