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While the world’s total urban population continues to grow, not all cities are witnessing such growth, some are actually shrinking. This shrinkage causes several problems to emerge including population loss, economic depression, vacant properties and the contraction of housing markets. Such problems challenge efforts to make cities sustainable. While there is a growing body of work on study shrinking cities, few explore such a phenomenon from the bottom up using dynamic computational models. To overcome this issue this paper presents an spatially explicit agent-based model stylized on the Detroit Tri-county area, an area witnessing shrinkage. Specifically, the model demonstrates how through the buying and selling of houses can lead to urban shrinkage from the bottom up. The model results indicate that along with the lower level housing transactions being captured, the aggregated level market conditions relating to urban shrinkage are also captured (i.e., the contraction of housing markets). As such, the paper demonstrates the potential of simulation to explore urban shrinkage and potentially offers a means to test polices to achieve urban sustainability.