The collection and trading market of calligraphy and painting in the Song Dynasty was relatively developed. This study aims to understand the role of painting establishments and painting academies in the creation and exchange of calligraphy and painting through an investigation of the entities that contributed to the painting market during this period. The article has searched and collected historical materials, poems, notes, painting theories, and other relevant materials from the Song Dynasty. Through the analysis of typical cases involving painting establishments and painting academies, it was found that in the Song Dynasty, the painting market was centered around these institutions, connecting painting artists, nobles, regular sellers, and market merchants to facilitate the trading and dissemination of calligraphy and painting. The prosperity of painting and calligraphy in the Song Dynasty was closely tied to the development of painting premises and painting academies. This article specifically focuses on the investigation of painting houses and the assessment system of painting academies, which played a significant role in promoting the trade of calligraphy and painting. Additionally, it examines the emergence of the "often sell" group in the middleman role of the calligraphy and painting trade during the Song Dynasty, which was distinct from the "tooth". This occupation made a substantial contribution to the circulation and prosperity of the calligraphy and painting market in the Song Dynasty.