Place-based GIS are at the forefront of GIScience research and characterized by textual descriptions, human conceptualizations as well as the spatial-semantic relationships among places. The concepts of places are difficult to handle in geographic information science and systems because of their intrinsic vagueness. They arise from the complex interaction of individuals, society, and the environment. The exact delineation of vague regions is challenging as their borders are vague and the membership within a region varies non-monotonically and as a function of context. Consequently, vague regions are difficult to handle computationally, e.g., in spatial analysis, cartography, geographic information retrieval, and GIS workflows in general. The emergence of big data brings new opportunities for us to understand the place semantics from large-scale volunteered geographic information and data streams, such as geotags, texts, activity streams, and GPS trajectories. The term "social sensing" describes such individual-level big geospatial data and the associated analysis methods. In this dissertation, I present a generalizable, data-driven framework that complements classical top-down approaches by extracting the representations of vague cognitive regions and function regions from bottom-up approaches using spatial statistics and machine learning techniques with various social sensing sources. I demonstrate how to derive crisp boundaries for cognitive and functional regions from points of interest data, and show how natural language processing techniques can enrich our understanding of places and form a foundation for the semantic characterization of place types and the generalization of regions. This work makes contributions to the development of computational methodologies for extracting vague cognitive regions and functional regions using data-driven approaches as well as the novel semantic generalization processing technique.