Art research has long aimed to unravel the complex associations between specific attributes, such as color, complexity, and emotional expressiveness, and art judgments, including beauty, creativity, and liking. However, the fundamental distinction between attributes as inherent characteristics or features of the artwork and judgments as subjective evaluations remains an exciting topic. This paper reviews the literature of the last half century, to identify key attributes, and employs machine learning, specifically Gradient Boosted Decision Trees (GBDT), to predict 13 art judgments along 17 attributes. Ratings from 78 art novice participants were collected for 54 Western artworks. Our GBDT models successfully predicted 13 judgments significantly. Notably, judged creativity and disturbing/irritating judgments showed the highest predictability, with the models explaining 31% and 32% of the variance, respectively. The attributes emotional expressiveness, valence, symbolism, as well as complexity emerged as consistent and significant contributors to the models’ performance. Content-representational attributes played a more prominent role than formal-perceptual attributes. Moreover, we found in some cases non-linear relationships between attributes and judgments with sudden inclines or declines around medium levels of the rating scales. By uncovering these underlying patterns and dynamics in art judgment behavior, our research provides valuable insights to advance the understanding of aesthetic experiences considering visual art, inform cultural practices, and inspire future research in the field of art appreciation.