Policy makers and practitioners are in need of useful tools and models for assessing ecosystem service outcomes and the potential risks and opportunities of ecosystem management options. We utilize a state-and-transition model framework integrating dynamic soil and vegetation properties to examine multiple ecosystem services—specifically agricultural production, biodiversity and habitat, and soil health—across human created vegetation states in a managed oak woodland landscape in a Mediterranean climate. We found clear tradeoffs and synergies in management outcomes. Grassland states maximized agricultural productivity at a loss of soil health, biodiversity, and other ecosystem services. Synergies existed among multiple ecosystem services in savanna and woodland states with significantly larger nutrient pools, more diversity and native plant richness, and less invasive species. This integrative approach can be adapted to a diversity of working landscapes to provide useful information for science-based ecosystem service valuations, conservation decision making, and management effectiveness assessments.