This doctoral thesis explores the agrarian development in 20th Estonia and the role of family farming during three major agricultural transformations. It consists of four papers and an introductory chapter for which the common departure are the situation appearing in the Estonian farming landscape after the regained independence in 1991. The first three studies analyse comparative aspects on Estonia's interwar experiences with focus on land reform, agricultural co-operation, and agricultural export development. The fourth study focuses on the role of private plots during the Soviet period and the conversion of these into subsistence holdings after 1991. By merging the perspectives in these papers, the introductory chapter explores the impacts and legacies of previous transformations on the post-Soviet agricultural transformation up to 2004. The thesis specifically analyses the long-term effects of perceptions of markets and the role of agricultural production, changes in the agrarian property relations, organisation of agricultural production and co-operation. In analytical terms, this is discussed from the perspectives of continuity and discontinuity. Besides the several societal changes affecting the agrarian property relations in 20th century Estonia, the radical and decisive shifts have also affected markets, trade and economic integration. Since the end of the First World War, Estonia has been quickly thrown between different economic-political systems and legal environments. From the perspective of the small state’s dependence on trade and reliance on a few markets, the upheavals in the early 1920s, after World War II, and not least the fall of the Soviet Union, Estonia’s long-term economic development has been significantly affected. In this context the role of agriculture has changed. Most important, however, this dissertation shows how the idea of small-scale family farming survived throughout the planned economic period and became an indispensable production unit, even though it turned out to be a myth as soon as the Soviet system was dissolved and the exposure to international competition began after 1991.