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This chapter presents projections of residential development in Wappinger Creek watershed of Dutchess County, New York in the Hudson River Valley. A spatial econometric model is developed based on data from a geographical information system (GIS) of county-level socio-economic trends, tax parcel attributes, town-level zoning restrictions, location variables, and bio-geophysical constraints including slope, soil type, riparian and agricultural zones. Monte Carlo simulation is employed to distribute spatially explicit projections of land-use change under various residential development scenarios. Scenario analysis indicates the likelihood of continued residential, decentralized development patterns in formerly agricultural and forested parcels. Policy scenarios demonstrate possible courses of action to direct development and protect watershed health.