The last decade has seen a relatively quiet revolution happening within historic preservation. The field experienced a steady increase in digital technologies to document the historic built environment. Many practitioners now have access to a suite of documentation methodologies that employ digital-based equipment and software (e.g., light detection and ranging [LiDAR], ground-penetrating radar [GPR], high-density laser scanning, digital photogrammetry). This access to new techniques has led to a shift in some of the research questions being investigated and the scale of the investigations. In this paper, we present case studies from our work in Charleston, SC, highlighting the application of digital technologies to the documentation of the historic built environment at two scales— the individual building and the landscape.