This study focuses on the role of multiple solution tasks (MST) incorporating multiple learning tools and representation systems (MTRS) in encouraging each student to develop multiple perspectives on the learning concepts under study and creativity of thought. Specifically, two types of MST were used, namely tasks that allowed and demanded multiple solutions and tasks that allowed but did not demand multiple solutions from each student. Each of these tasks was tested in the field using 14-year-old students, through a comparative experiment on the learning of the mathematical notion of area within the C.AR.ME computer microworld that provides MTRS for the learning of area. Data analysis reveals that all students who were asked to encounter tasks allowing and demanding multiple solutions within C.AR.ME were motivated to invent a plethora of solution strategies to these tasks, by integrating both their intuitive and school-based knowledge with the knowledge embodied within C.AR.ME, and to construct diverse perspectives on the concepts in question which are non-common to paper-and-pencil and school practices. On the other hand, students expressed limited views on these concepts when faced with tasks that allowed but did not demand multiple solutions.