The present study compares trends in vegetation quality observed from 1975 to 2000 in two Mediterranean cities (Athens and Rome) with the distribution and density of urban settlements in 2010 to test if urban sprawl was preceded by changes in landscape characteristics. These cities are characterised by unregulated expansion and similar long-term population dynamics, but possess different urban forms. The results indicate that changes in vegetation quality are correlated with the type of urban development found around the two cities. In particular, it was found that (i) dispersed settlements are more likely to be located on land of higher vegetation quality than compact settlements and (ii) land with stable vegetation quality over time was primarily associated with compact settlements, while land with both increasing and decreasing vegetation quality was associated with low-density, dispersed settlements. In 2010, low-density, dispersed settlements were concentrated in areas associated with decreasing vegetation quality between 1975 and 2000. Trends in vegetation quality could thus be a proxy indicator of urban sprawl in the Mediterranean region.