The Processing Fluency Theory posits that the ease of sensory information processing in the brain facilitates esthetic pleasure. Accordingly, the theory would predict that master painters should display biases toward visual properties such as symmetry, balance, and moderate complexity. Have these biases been occurring and if so, have painters been optimizing these properties (fluency variables)? Here, we address these questions with statistics of portrait paintings from the Early Renaissance period. To do this, we first developed different computational measures for each of the aforementioned fluency variables. Then, we measured their statistics in 153 portraits from 26 master painters, in 27 photographs of people in three controlled poses, and in 38 quickly snapped photographs of individual persons. A statistical comparison between Early Renaissance portraits and quickly snapped photographs revealed that painters showed a bias toward balance, symmetry, and moderate complexity. However, a comparison between portraits and controlled-pose photographs showed that painters did not optimize each of these properties. Instead, different painters presented biases toward different, narrow ranges of fluency variables. Further analysis suggested that the painters' individuality stemmed in part from having to resolve the tension between complexity vs. symmetry and balance. We additionally found that constraints on the use of different painting materials by distinct painters modulated these fluency variables systematically. In conclusion, the Processing Fluency Theory of Esthetic Pleasure would need expansion if we were to apply it to the history of visual art since it cannot explain the lack of optimization of each fluency variables. To expand the theory, we propose the existence of a Neuroesthetic Space, which encompasses the possible values that each of the fluency variables can reach in any given art period. We discuss the neural mechanisms of this Space and propose that it has a distributed representation in the human brain. We further propose that different artists reside in different, small sub-regions of the Space. This Neuroesthetic-Space hypothesis raises the question of how painters and their paintings evolve across art periods.