As scientific data repositories and filesystems grow in size and complexity, they become increasingly disorganized. The coupling of massive quantities of data with poor organization makes it challenging for scientists to locate and utilize relevant data, thus slowing the process of analyzing data of interest. To address these issues, we explore an automated clustering approach for quantifying the organization of data repositories. Our parallel pipeline processes heterogeneous filetypes (e.g., text and tabular data), automatically clusters files based on content and metadata similarities, and computes a novel "cleanliness" score from the resulting clustering. We demonstrate the generation and accuracy of our cleanliness measure using both synthetic and real datasets, and conclude that it is more consistent than other potential cleanliness measures.