Agricultural land extent and change information is needed to assess food security, the effectiveness of land use policy, and both environmental and societal impacts. This information is especially valuable in biodiversity hotspots such as the Mediterranean region, where agricultural land expansion can result in detrimental effects such as soil erosion and the loss of native species. There has also been a growing concern that changing agricultural extent in fire-prone regions of the Mediterranean may increase fire risk due to accumulation of fuel in abandoned areas. In this study, we assessed the extent and change of agricultural land in Southern Greece from 1986 to 2020 using a combined European Land Use/Cover Area frame Survey (LUCAS) and Landsat time series approach. The LUCAS data and Landsat spectral-temporal metrics were used to train a random forest classifier, which was used to classify arable land and permanent agriculture (e.g., olive orchards, vineyards) at annual time steps. A post-processing step was taken to reduce spurious landcover class transitions using transition likelihoods and annual class membership likelihoods. A validation dataset consisting of 2666 samples, identified via a stratified random sampling approach and high-resolution imagery and time series analysis, were used to evaluate stable and change strata accuracies. Overall accuracies were greater than 70% and strata-specific accuracies were highly variable between stable and change strata. The results show that southern Greece has experienced a recent gain in arable land (~12,000 ha from ~2009–2020) and a much larger gain in permanent agriculture (>115,000 ha from ~1993–2020). Arable land loss mainly occurred from 1987 to ~2002 when extent decreased by 15,000 ha, of which 66% was abandoned. The semi-automated approach described in this paper provides a promising approach for monitoring agricultural land change and enabling assessments of agriculture policy effectiveness and environmental impacts.