This paper attempts to discuss Heidegger's thinking trajectories and shift on dwelling and space. I start from Being and Time by viewing spatiality of Dasein, thing and world, and then deal with the importance and meaning of dwelling in his later thought by pointing out issues of human being's possible living and destiny in a world dominated by technology. However, in spite of Heidegger's thinking has inspired researchers on human geography and architecture, aspects of social, political and cultural context of dwelling and space have been neglected.