Land-use intensification in agroecosystems has led to population declines in many taxonomic groups, especially farmland birds. Two contrasting conservation strategies have therefore been proposed: land sharing (the integration of biodiversity conservation in low-intensity agriculture) and land sparing (the spatial separation of high-yielding agriculture and areas for conservation). Despite the large academic interest in this field, only few studies have taken into account stakeholders’ perspectives of these strategies when assessing conservation implications. We modeled the effects of three land-use scenarios (a business-as-usual, a land-sharing, and a land-sparing scenario), developed together with regional stakeholders, on the habitat area of 13 regionally endangered bird species in the Middle Mulde River Basin (Saxony, Germany). We used random forest models based on environmental variables relating to land-use/cover, climate and soil characteristics, occurrence of linear landscape elements (hedges and tree rows), and distance to water and major roads. Responses to the three land-use scenarios were species-specific, but extensively managed permanent grassland and the density of forest edges were positively associated with the occurrence of most bird species. Overall, the land-sharing scenario provided the largest breeding habitat area: 76% of the species had a significant (p < 0.05) increase in breeding habitat, and none showed a significant decrease. Our findings confirm that balancing the different, often contrasting habitat requirements of multiple species is a key challenge in conservation and landscape management. Land sharing, which local stakeholders identified as the most desirable scenario, is a promising strategy for the conservation of endangered birds in agricultural landscapes like our study region.