The purpose of this study is to investigate the effects of restricting children’s free play on children’s levels of pretend play. The level of play restriction was examined using the following: How many children can play in the same area of interest, freedom of using toys, the space available for play, and time limitation. The participants for this study were selected through two screening steps. First, a questionnaire concerning the extent of free-play restriction was sent out to 90 teachers in Korea. Of these teachers, two teachers with a high degree of limitation and two teachers with a low degree of limitation were chosen. Second, the 60 children from the classrooms of the 4 chosen teachers were observed in order to measure their levels of pretend play. The results of this study found children who were under the care of the teachers with a low degree of limitation engaged in pretend play more frequently, demonstrated a higher degree of make-believe actions and subjects, and played in more diverse areas of interest than the children under the care of the more limiting teachers. This study emphasizes the importance of providing children with an environment where they can play freely.