Globally, increased investor interest in land is confronting various types of political mobilisations from communities at the grassroots level. This paper examines the case study of a land occupation movement called Chengara struggle in the largest corporate plantation in southern India. The movement is led by the historically dispossessed scheduled caste and scheduled tribe communities. The objective of the study is to understand the type of institutional transformation of property rights that the movement is calibrating. Institutional theory is used to determine the nature and direction of transformation using the framework of economic and political transaction costs. The paper concludes that the central demand of the struggle for individual title deed has higher private gains for right-holders, but overall negative gains for agricultural productivity. The paper concludes that productivity-oriented demands to restructure land-use rights within plantations might converge in the land struggles of the future.