Play is fundamental to children’s physical growth, social development, and mental and emotional well-being; and how we plan, and design high-rise housing estates impacts children’s ability to access and use spaces for play, thus impacting their overall growth and development. By using Lefebvre’s Spatial Triad (1974/1991) as an analytical framework, this paper investigates (1) ‘Conceptualized Space’ or ‘play areas and materiality of the play areas as conceptualized by design professionals’; (2) ‘Actual Space’ or ‘spaces where children actually play’; and (3) ‘Experienced Space’ or ‘caregivers’ assessment of play spaces and their preferences of play materials, elements and surfaces for young children in high-rise housing estates. Comparative case-study research of seven housing estates from a baseline study of 63 high-rise housing estates was adopted to realize contrasts, patterns, or similarities across the cases. Methods included (1) semi-structured open-ended interviews with design professionals including developers (n=4), architects (n=4), landscape architects (n=2) and play equipment manufacturer (n=1); (2) In-depth field studies; and (3) semi-structured open-ended interviews with parents (n=27), grandparents (n=5) and nannies (n=4) of young children. This study generates new knowledge about design and planning considerations for designated play spaces, caregivers’ and designers ideas around nature based play, caregivers’ preferences of play elements, materials and surfaces, and details spatial factors influencing young children’s play areas in housing estates. As a way forward, the paper offers 11 guidelines to influence the design and planning of play spaces and open areas in future housing estates to fulfil young children’s play needs.