This paper analyzes the location, landscape elements, and outdoor space composition in the Korean Sosu seowon and Chinese Bailudong seowon. The Sosu and Bailudong seowons were designed to fit well into similar valleys, and they share the approach of Jwa hak woo myo, which means the sacrificial space is on the right and the educational space is on the left. The two seowons each have unique layout characteristics, which reflect topographical features. In the case of the Sosu seowon, the buildings have different orientations, creating a natural arrangement of structures. By contrast, in Bailudong seowon, buildings have a fixed orientation and a formal serial-parallel arrangement along five abscissa axes and one longitudinal axis. Pedestrian systems were established in both seowons, designed to reflect the hierarchical order of the buildings. The Sosu seowon adopted the pedestrian system that encouraged strolling, while the Bailudong seowon’s orthogonal circulation system was set up lengthwise, in parallel with the transverse. The component buildings used for worshiping ancestors and giving lectures, as well as the supporting spaces, were created at the start of the building process, while various other buildings were built to meet the needs of later periods. The two waterscape facilities are also very different: the Takcheongji (pond) at the Sosu seowon symbolizes clarifying the mind through study, while the Panchi (pond) at the Bailudong seowon merges with the Lishengdian (shrine) to contain and represent Confucian culture. The rock carvings at the two seowons differ in both quantity and content. However both sets of rock carvings incorporate Neo-Confucian meanings designed to encourage students to cultivate themselves. From the perspective of earlier literature, both seowons took the meaning of trees very seriously, although they planted different types of trees in their grounds.