In many agricultural landscapes, roadside (or road verge) environments provide important refuge for threatened native species and ecosystems, and are often selected as benchmark sites to guide restoration activities. However few studies have investigated potential temporal variability in roadside vegetation conditions. In this paper we used archived cadastral maps to determine road age and examine potential variability in roadside vegetation structures in a typical rural landscape in south-eastern Australia. We found significant differences in the density of mature trees for road segments in different road-age categories. The oldest roads (<1870s) were characterized by having the greatest density of large hollow-bearing Eucalyptus trees, but few native conifer trees or shrubs. Roads surveyed when broad-scale clearing commenced (1870–1879), and not the oldest roads, were found to be more intact in terms of the density of large pre-settlement trees, range of tree stem-size classes and overall shrub diversity. By contrast, the youngest roads (post-1900s) had the greatest number of native conifer trees, but few shrubs or large Eucalyptus trees. As a result, roads of different ages had different densities of hollow-bearing trees, which is discussed in terms of past land-use legacies. These results have important implications for selecting roadsides as benchmark sites for restoration activities, and highlight the critical importance of roadsides to conserving native biota in agricultural landscapes.