Infill redevelopment—the transformation of previously used urban sites—is generally regarded as an important way to attain environmental and urban sustainability goals. At many locales, however, such urban renewal, community development, and tax revenue goals must be reconciled with historic preservation objectives. Are economic incentives and regulatory relief useful tools for encouraging reuse of abandoned or underutilized urban sites with historic buildings? Answering this question is of key importance for many European cities and for older US cities, and has important implications in terms of urban sustainability and “smart growth” initiatives. We use conjoint choice experiments to explore the relative importance of economic incentives, regulatory relief, land use and property regime offerings at underutilized historical sites in Venice, Italy. We survey real estate developers and investors, and ask them to choose between pairs of hypothetical projects in three Venice locations, as well as between one of these projects and the alternative to do a development project elsewhere. Statistical models of the responses to these choice questions indicate that respondents are sensitive to the price of acquiring the land (and hence to any policies that influence prices), and especially sensitive to the property regime that would be granted to developers and investors and to the allowable land use. Contrary to expectations, our respondents were insensitive to tightening or relaxing the stringency of building conservation restrictions. Our findings sound a common theme with Howland (2004), who warns that redevelopment of previously used sites in Baltimore is impaired by obsolete land uses, zoning and infrastructure (but not by suspected or actual contamination). We conclude that the City should focus on offering land uses and property regimes that are more in tune with developer demand.