In Ireland, native and semi-natural woodlands dominated by native tree species occupy only a small proportion of the landscape and are highly fragmented. Recent expansion of these woodlands has been driven largely through native woodland afforestation schemes targeting different woodland habitat types according to soil and landscape context. Despite ongoing expansion of such tree-planting initiatives, systematic ecological monitoring of recently afforested native woodlands, largely established on private farmland, remains limited. This study evaluates early ecological trajectories of native woodland plantations and examines site-and landscape scale factors influencing plant community assembly and habitat development. Vegetation composition and structure were surveyed across a 20-year chronosequence of 47 native woodland plantations in agricultural landscapes of eastern and midland Ireland. Species richness was modelled to identify key environmental predictors, with patterns further elucidated through analysis of species composition and trait-environment relationships. Habitat trajectories were then assessed by comparison with National Forest Inventory reference conditions and vegetation community classification. Plant communities showed a clear temporal shift from grassland dominated assemblages to woodland vegetation with increasing stand age, shaped by landscape context. Most older stands aligned with their intended woodland vegetation communities, indicating positive restoration trajectories, while natural colonisation of native tree species increased with stand age, suggesting that tree planting does not preclude opportunities for a degree of process-driven restoration. Overall, results indicate that planted native woodlands can progress towards target woodland habitats within two decades, highlighting the potential for native afforestation on agricultural land to contribute to the expansion of biodiverse and resilient woodland networks within modified landscapes. These findings are also relevant to emerging forest and ecosystem restoration objectives under the EU Nature Restoration Law.