The article considers selected methodological approaches to the study of learning environments, which include socio-psychological, spatially-substantive, pedagogical ("environmental approach in education"), and the ecological-psychological approaches. The author proposes pedagogical typology of learning environments based on the works of J. Korczak, considering the environments in the context of actualization of a personal freedom and activity of pupils and students in these environments. Thus, in this context the author considers dogmatic, career, creative and serene kinds of environment. The author presents the proprietary methodology of vector simulation of the learning environments.The results of empirical research of a qualitative and quantitative assessment of learning environments by high school and college students are considered. Systemic problems in the achievement of the pedagogical effectiveness of the school and university environments, as well as the contradictions of succession between school and university learning environments are revealed. It is found that high school students assess the school environment primarily as a "career", while the junior students mostly perceive the university environment as "dogmatic". Thus, when moving from a school environment to a university environment, a reduction in personal developmental potential of the learning environment was noted in terms of actualization of students' creative freedom and activity. According to students' assessments, personal developmental potential of the university environment is restored in senior students due to their involvement in research and project activities of the university.