Results/Conclusions: Afforested woodlands, pine plantations and grassy fields differed significantly in their average species richness, native species richness, prairie-savanna indicator species richness and indices of floristic quality. As indicated by all four variables, afforested woodlands had the highest conservation value and grassy fields the lowest. The results of multi-response permutation procedures indicated that edge-effects had a detectable influence on herbaceous plant community composition to a distance of less than 10 m from the habitat edge in afforested woodlands and pine plantations. There was no significant change in herbaceous composition from habitat edge to interior for weedy fields. Relative dominance of native species and indices of floristic quality significantly increased from the habitat edge towards the interior for both afforested woodlands and pine plantations. But the frequency of prairie-savanna indicator species, which were historically dominant in the landscape, was greater at the edges of woodlands than the interior. Canopy cover and soil variables were significantly correlated with patterns of herbaceous species composition both between and within sites. Our results suggest that plant conservation efforts on participating farms should prioritize afforested woodlands. We suggest that gradually opening the canopy toward the interior of afforested woodlands might promote the inward recolonization of prairie and savanna species that are currently more frequent at habitat edges. Any restoration plan should be adaptive, however, as there is a significant risk of promoting the spread of invasive species.