We study how deep learning can improve valuation in the art market by incorporating the visual content of artworks into predictive models. Using a large repeated-sales dataset from major auction houses, we benchmark classical hedonic regressions and tree-based methods against modern deep architectures, including multi-modal models that fuse tabular and image data. We find that while artist identity and prior transaction history dominate overall predictive power, visual embeddings provide a distinct and economically meaningful contribution for fresh-to-market works where historical anchors are absent. Interpretability analyses using Grad-CAM and embedding visualizations show that models attend to compositional and stylistic cues. Our findings demonstrate that multi-modal deep learning delivers significant value precisely when valuation is hardest, namely first-time sales, and thus offers new insights for both academic research and practice in art market valuation.