This study examines the vernacular wooden architecture of Gilan, Iran, and Shikoku, Japan. Both regions are located in a humid subtropical climate with vast forests and timber resources. Although far apart, Gilan and Shikoku were shaped by comparable environmental conditions, resulting in architectural parallels and climate-driven tectonics. One of the main shared characteristics is elevated wooden foundations. This study uses a comparative approach, employing structural and spatial analysis. By analyzing case studies from the Gilan Rural Heritage Museum and the Shikoku Mura Museum with elevated wooden foundations, this research identifies other key architectural features, including steep gabled roofs and extensive use of unprocessed natural materials. In Gilan, local “shikili” houses are characterized by wooden structures resting on pyramid-like individual foundations (pakeh), thick mud-plastered and wooden walls, and expansive semi-open porches (telar), which are the main living space and surround the central rooms of the building. Shikoku’s structures, while also elevated, rely on complex wooden joinery techniques such as stepped dovetailed splice (koshikake aritsugi), stepped gooseneck splice (koshikake kamatsugi) and groundsill joint (dodai shiguchi), showcasing advanced craftsmanship rather than mass production, which is also employed in the construction of wooden panel walls. Both regions presented architectural types suited to the regional environmental conditions; however, there were some differences in structural character, material use, and spatial organization. This study explores how understanding vernacular contexts leads to convergence and divergence in architecture while also demonstrating the preservation of local crafts.