Abstract: Systems and methods for automatically generating an art index. The method is both sympathetic to the individual characteristics of art—a hedonic approach—and accurate in tracking changes in price over time—a repeat sales approach. Artworks with similar core characteristics are organized into groups according to their specific criteria. The characteristics include genre, date range, content, materials, size, coloration, style, and other characteristics. Following these guidelines, the system is able to generate hundreds of thousands of ever-increasing datasets, providing the statistical foundation required to derive accurate indices, while remaining true to the unique nature of art. The system is also operative to generate various types of reports.