Across Africa there has been a growth in medium-sized farms, including in Zimbabwe following the land reform of 2000. What are the prospects of such farms driving new forms of agricultural commercialization? In this article we seek to learn lessons from the past by examining the experience of ‘native purchase areas’, which were established from the 1930s in Zimbabwe. Through a detailed historical study of Mushagashe small-scale commercial farming area in Masvingo Province, the article explores the changing fortunes of farms over time. Historical information is complemented by a survey of twenty-six randomly selected farms, examining patterns of production, asset ownership and accumulation. In-depth interviews explore life histories and changes in social arrangements that have influenced agrarian change. Four broad farm types are identified, including those that are commercialized, projectized, villagized, and held or abandoned. These categories are not static, however, and the article emphasizes non-linear patterns of change. Following Sara Berry, we show how pathways of commercialization are diverse and unpredictable, influenced by interlocking conjunctures of social dynamics, generational changes and political-economic conditions. Commercialization outcomes are dependent on the intersection of relational dynamics and more structural, political economy factors. Bursts of commercialization on these farms are contingent on access to employment by farm owners, labour (hired, squatters and offspring) and, perhaps above all, money to invest. The much-hyped policy vision of a new medium-scale commercial farm sector emerging in Africa therefore must be qualified, and divergent outcomes recognized.