In the 1970s, cities across the country began implementing urban homesteading programs, in which they transferred surplus vacant housing units to hopeful homeowners for the low cost of $1 and a two-year commitment to rehabilitating and occupying the unit as a primary residence. The goals of these programs were varied, but typically included neighborhood stabilization, affordable housing, and incentivizing the return of wealthier households back to urban neighborhoods. This thesis argues that, while homesteading programs achieved mixed results in regards to these goals, they did achieve historic preservation outcomes. In order to support this proposition, this thesis examines the history of homesteading in Baltimore City, Maryland. Although Baltimore was not the first city to launch a program, it was the most influential and its program had long-lasting impact. Baltimore pursued two different approaches: scattered-site and neighborhood-wide homesteading. Based on archival research, interviews, and site visits, this thesis finds that the former often created home ownership opportunities for more moderate-income households, and that the latter achieved significant preservation outcomes. This thesis also argues that, given the ongoing loss of population in many Rust Belt cities; the nationwide abundance of housing abandoned following the foreclosure crisis; and the simultaneous shortage of affordable housing opportunities, the time is ripe for homesteading programs to be re-examined. Preservationists should recognize homesteading as a powerful tool for vernacular preservation, and join planners and affordable housing advocates in promoting the potential for homesteading to address many urban challenges at once.