The thesis develops an empirically tested analytical framework which links value theory with planning and design practices to investigate context-specific spatial transformations as a result of individual and collective value judgements. Four key aspects of water values including flood safety, as well as economic, social and environmental values, are studied, and their interrelationships are discussed. Morphological analyses and value assessments are conducted to explore in what sense spatial changes can be considered an expression of the changing values and what we can learn from it to deal with complex spatial situations. The empirical studies are based on the long-term spatial development of Guangzhou as representative of a historical and rapidly growing delta city in China. Three development stages are illustrated to show different patterns of water-city interactions, the waterways city (before the 1920s) that was mainly structured by natural forces including natural waterways, the functional city (1920s-1970s) that was managed in a highly centralised approach such as functional zoning and large-scale flood defence, and the pluralistic city (after the 1970s) with the tendency towards accommodating plural values of water such as environmental sustainability, social equity and cultural identity.