As early as the 1640s, the Dutch colonists constructed a main road from the Zeelandia (Tainan area) down south to the Hengchun peninsula, passing through tribal settlements of Wandan (called the Lower Danshui tribe) and Fangsuo, in order to pacify the eastern parts of tribal groups and searching for gold mines. During the Qing era, Wandan village emerged as the major trading post of rice and sugar, which attracted numerous merchants to set up shops there. At the same time, the government also established civil and military bureaus for collecting land tax and maintaining law and order, paving for the emergence of Wandan Street as the epic center of the Pingtung plains. Through analyzing the land documents of a local landlord family, this article traces the historical development of Wandan village-street, which reveals various patterns of land occupation, including absentee landlords and localized merchants. It also shows the changing fate of different religious organizations, and their functions as the focus of self defense group as against the threat of the nearby Hakka militia. Finally and most importantly, the article analyzes the complex land deals between the native tribal people and the Han Chinese merchant-landlords. It reveals the eventual dispersion of these tribes toward the mountainous areas and hence become marginalized in Han Chinese society.