Drawing on fieldwork that incorporates ethnography and archival land research, this dissertation investigates the transformation of land into property in Hawai’i and its continued impact on the development of Hawaiian landscapes and communities contemporarily. On the windward side of the North Shore of O‘ahu, Hawai‘i, residents have been fighting against the threat of commercial and urban development for decades. Through interviews with key community leaders, I describe the origins of the current grassroots anti-development movement that started in the 1970s, when protestors first organized around the protection of Native Hawaiian and non-Indigenous farmers being threatened with eviction to make way for urban development. The colonial and foreign influence on the privatization of property in the 1850s had set into motion legal practices of land dispossession that continue to impact the contemporary land struggles over development on the North Shore today. I demonstrate that the adoption of Western legal attitudes towards the productive capacity of land and property ownership is what has allowed for affluent prospectors to amass large estates over time, resulting in the immense loss of Native Hawaiian-held kuleana properties to powerful developers through processes of anticommoning. With this dissertation, I conduct a novel analysis of the ways in which this legal doctrine is inherently unsuited to address both real and intangible non-Western patterns of property distribution, thereby creating both land and resource insecurities characteristic of a tragedy of the anticommons. In conclusion, I argue that these practices ultimately undermine residents’ decision-making power over the direction of their community and their ability to resist unwanted development interventions in the future.