Institutional settings play a key role in shaping land cover and land use. Our goal was to understand the effects of institutional changes on agricultural land abandonment in different countries of Eastern Europe and the former Soviet Union after the collapse of socialism. We studied ∼273 800 km2 (eight Landsat footprints) within one agro-ecological zone stretching across Poland, Belarus, Latvia, Lithuania and European Russia. Multi-seasonal Landsat TM/ETM + satellite images centered on 1990 (the end of socialism) and 2000 (one decade after the end of socialism) were used to classify agricultural land abandonment using support vector machines. The results revealed marked differences in the abandonment rates between countries. The highest rates of land abandonment were observed in Latvia (42% of all agricultural land in 1990 was abandoned by 2000), followed by Russia (31%), Lithuania (28%), Poland (14%) and Belarus (13%). Cross-border comparisons revealed striking differences; for example, in the Belarus–Russia cross-border area there was a great difference between the rates of abandonment of the two countries (10% versus 47% of abandonment). Our results highlight the importance of institutions and policies for land-use trajectories and demonstrate that radically different combinations of institutional change of strong institutions during the transition can reduce the rate of agricultural land abandonment (e.g., in Belarus and in Poland). Inversely, our results demonstrate higher abandonment rates for countries where the institutions that regulate land use changed and where the institutions took more time to establish (e.g., Latvia, Lithuania and Russia). Better knowledge regarding the effects of such broad-scale change is essential for understanding land-use change and for designing effective land-use policies. This information is particularly relevant for Northern Eurasia, where rapid land-use change offers vast opportunities for carbon balance and biodiversity, and for increasing agricultural production on previously cultivated lands.