This study investigates the affordances of cul-de-sac as play space in Malaysian urban neighbourhood for middle childhood children. Behavioral responses of 82 children experiencing two cul-de-sac in two different residential neighbourhoods were elicited using three methods: semi-structured interviews, observations and survey questionnaire. It is found that cul-de-sac with a monotonous, flat landscape with some vegetation offered less affordances to the children than the one that is a slightly slopping landform with a variety of vegetation. In addition, it is not the aesthetic design of the cul-de-sac but the caregiver’s permission and the affordances of sociality that encourage the children to play.