Using a variety of new sources directly pertaining to different types of rural estate, and contrary to interpretations of rural Chile as a traditional society the affected by economic modernisation, this article analyses the transition of the hacienda system in central Chile towards agrarian capitalism during the period of export-led growth from the 1860s to 1930. It argues that the expansion of the 'landowner enterprise', along with developments in mechanisation and irrigation, resulted in the marginalisation of the precarious 'peasant enterprises' operated by tenants and the gradual proletarianisation of the agricultural workforce. The development of agrarian capitalism transformed the collective action of rural workers, which assumed modern forms such as strikes and unionisation, and thus became significant in national politics. The first wave of rural conflicts, which took place in the early 1920s, can therefore be understood as the response of the emerging rural working class to the agrarian expansion that Chile experienced as part of the process of capitalist modernisation.