This study aimed to quantify and analyze the productivity, profitability and sustainability of alternative land uses in the degraded grasslands using a bioeconomic modeling approach. It was conducted in Claveria, Misamis Oriental in Mindanao, the Philippines. Results of bioeconomic analysis showed that tree-based land use systems have significantly higher financial profitability and environmental benefits. The latter were measured in terms of higher carbon sequestration, least soil erosion, and sustained soil nutrients relative to current farmers’ practice of maize cropping. Despite these, survey results showed the extent of tree farming remains low (<10 percent of land area). The risk analysis indicated that while timber-based systems earned the highest net present value (NPV), they seemed to be the most risky options as reflected by the high coefficient of variations of the NPV ranging from 164 percent to 205 percent. The study recommended measures to reduce price risk and the need to improve risk management capability of farmers to promote expansion of smallholder tree farming. Provision of relevant and timely price information and price risk insurance are such possibilities. It is also suggested that payments to farmers for environmental services like carbon sequestration be explored to encourage expansion of tree-based land use systems.