Neoliberal agricultural frontiers create paradoxes for modern rural landscapes and populations as global biodiversity conservation efforts and commodity food chains increasingly structure land ownership, social relations, economic opportunities and land use decisions. In the northern borderlands of Costa Rica, in the San Juan La Selva Biological Corridor, there has been an accelerated history of agrarian change beginning with a land rush and deforestation, then the institution of strict conservation laws, a forest transition and now, the rapid expansion of pineapple cultivation amidst a growing non-farm economy increasingly based on ecotourism. This landscape presents the paradoxes of neoliberal rural development juxtaposing biodiversity conservation, agricultural industrialization and the non-farm economy as contested discourses that shape the lives and landscapes of rural populations. A political ecology and mixed method approach demonstrate the patterns of inequality at a landscape scale as well as provide a more detailed narrative of the diversity of rural livelihoods and how they are connected to distal global forces. Through in-depth interviews and household surveys conducted over 2012 this paper discusses agrarian change and the state of economic development as it is experienced and materially realized by the people who live and work in this landscape. Profiles of pineapple company managers, ecotourism lodge owners, small farmers, and Nicaraguan wage laborers are contrasted to reveal how gender, ethnicity and class relations are negotiated in this modern agricultural frontier and how the geography and development of this landscape are contested from these diverse perspectives and lived experiences.