Digitalization of learning attempts to be one of the key focuses of contemporary research in various fields of science, such as pedagogy or developmental psychology. The paper provides an overview of pedagogical outcomes of redesigning learning space in literature, history and culture in the framework of digital learning environments. The paper attempts to analyse the online educational platform "Education on Screen" in order to establish the key principles of designing effective digital learning spaces. At the same time, the paper examines the platform "Education on Screen" as a step towards digitalization of learning in the context of literature, history, social science and culture learning practices. The basis of the study presented in the paper lays in the integration of pedagogical and semiotic approaches, using the empirical research of Lev Vygotsky (1978, 1991) and his contribution in the field of pedagogical and developmental psychology as well as in the use of signs as pedagogical tools in learning. The online learning platform "Education on Screen" has been analysed in order to evaluate its pedagogical outcomes and provide useful principles of designing a contemporary digital space in literature, history, social science and culture. The approach used on a digital platform 'Education on Screen' attempts to prove itself an effective way of organizing learning space in order to make learning on the one hand attractive for contemporary school students by using familiar digital forms and, on the other hand, making learning process interactive, organizing creative learning environment and motivating a learner towards the self-development.