The effects of city decentralization and counter-urbanization of the American landscape have resulted in simultaneous negative impacts on both historic structures and agricultural landscapes. Rapid conversion of farmland has helped to facilitate the relocation of both populations and commercial activities in communities across the United States, leaving inner cities replete with functionless, unused, and unmaintained heritage structures. As civic core areas have become shells of their former selves, many once-vital structures have been removed while others have been abandoned and left to decay—a process known as demolition by neglect. While historic preservation efforts have attempted to salvage these historic structures, these efforts have initially focused on the preservation of each buildings individually, based on its historical value and architectural merit, not taking into account its role in a constantly changing contextual landscape. Attempts to counteract this process and the negative effects of fringe developments through land preservation have also gained momentum since the 1970s. In response to growing concerns about the climbing rate of neglected historic structures, this dissertation considers the factors that affect ways to measure and sustain the viability of these structures while also protecting their historical integrity. Using multiple case study comparisons based on indicators obtained from viability and historic integrity models, this study compares the characteristics of demolition by neglect of living heritage sites within colonial towns to determine whether the preservation of peripheral agricultural lands has aided in decreasing the rate of this neglect.