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Ecosystem services, essential for supporting life, are increasingly being altered by anthropogenic activities. This study focuses on the Cross Timbers ecoregion of the southern Great Plains, USA, where oak woodland and grassland co-exist. However, grasslands are rapidly transitioning to woodlands through a process known as woody plant encroachment, or are being considered for switchgrass biofuel production. Our objectives were to quantify the supporting (plant biodiversity, aboveground net primary productivity), provisioning (water quantity, forage production), regulating (soil organic carbon, flood regulation), and cultural services (hunting-based recreation, aesthetics) of four land use types—tallgrass prairie, oak woodland, eastern redcedar woodland, and switchgrass biofuel production—using the Millennium Ecosystem Assessment Framework. We integrated these services into an ecosystem sustainability index. Results showed that tallgrass prairie provided balanced services and ranked highest in this index. Eastern redcedar and switchgrass exhibited an imbalance in services, while oak woodland’s ranking varied with normalization methods. Our results highlight the need for grassland conservation by curtailment of eastern redcedar expansion. While oak woodland ranks high in cultural services, its restoration is recommended to enhance multiple ecosystem services. This study provides a roadmap for quantitatively evaluating ecosystem services to inform management decisions for ecosystem transitions and promote regional sustainability. Future research should broaden stakeholder engagement and explore integrated land use strategies within large watersheds encompassing multiple land uses to enhance regional environmental sustainability.