Visual arts education has been significantly influenced by technological progress and attracted significant research attention. This study focuses on how the exploration of visual arts in a digital environment (art software) shapes new ways for children to improve their visual literacy and social skills. The study followed a mixed methodology design that included observations, tests, children’s digital creative works, and works with ordinary materials. A 3-month intervention was implemented with a class of 21 primary students (12 years of age) and 1 teacher in Greece. Each week, students were introduced to, and explored, works of art (paintings of the late nineteenth to early decades of the twentieth century) through an educational art software application specially designed for this intervention. Students were engaged with interactive activities using the computer and learned to critically observe and understand the aesthetic characteristics of the paintings. Through a process of thoughtful dialogue and writing routines, students enhanced their visual perception and expressed their judgments about the aesthetic value of the observed artworks. Additionally, students designed and created their individual or collective pieces of art with digital and physical means. Findings suggest that the intervention had a positive influence on students’ creative engagement and aesthetic perception and value of artworks and on promoting peer collaboration. Overall, the study offers useful insights for teachers on how to efficiently integrate technology into visual arts education to support children in becoming informed citizens, critical consumers, and creative producers in this highly visual information age.