Abstract: As China’s urbanization shifts from incremental expansion to stock-quality improvement, the transfer of land development rights (TDR) has received renewed recognition as a spatial policy tool for optimizing territorial development efficiency and promoting the integration of urban and rural factors. Yet its transaction scale and effectiveness have consistently fallen short of the ideal scenario. Drawing on new institutional economics, this paper examines the cost-benefit constraints embedded in TDR institutions. It argues that the core bottleneck is how to improve the exchange benefits and use benefits of land use while reducing information-matching costs, negotiation and decision-making costs, and supervision and enforcement costs in land transactions. Moving beyond the “market trap” and “social overdraft” found in Western and Chinese practices, the analysis of the “enclave pooling” project in Dayun Town, Jiaxing, shows that multi-actor resource pooling and shareholding cooperation, together with government-coordinated asset-based dividends and targeted land allocation, can effectively dissolve multi-dimensional transaction costs, improve the dual benefits of land, and realize the plural value of TDR. From a cost-benefit perspective, the paper then discusses optimization strategies for TDR mechanisms, providing theoretical and practical references for high-quality territorial spatial development.