The past decade has seen several African countries increasing their agricultural growth, a trend largely underpinned by increases in land area cultivated instead of productivity increases. Meanwhile, scholars debate whether Africa should pursue a strategy of large-scale or smallholder farms, paying little attention to a special group of smallholder farmers who have transitioned to become medium- and large-scale farmers. This study, therefore, begins to analyze this group of farmers, using qualitative data from in-depth interviews and focus group discussions in Ghana. We analyze their characteristics, ingredients of farm-size expansion, and commercialization. Numerous insights are gained and hypotheses formulated for future research. One important insight is that with the right attitude, exposure, and discipline, it is possible for smallholder farmers to increase their farm size and commercialize regardless of initial farm enterprise choice. However, to transition, initial farm size and farming system appear critical, with farmers in areas of low population density and flat topography more likely to acquire larger farming land. The transition, however, occurs gradually over 20 to 30 years, with mean annual land acquisition rates ranging from 0.3 to 24.3 acres per year. In the transition process, large- and medium-scale farmers are found to increase their use of modern farm inputs (such as fertilizer and high-yielding seed varieties) and agricultural technologies (such as tractors and processing machinery) and appear more productive than smallholder farmers. Additional quantitative analyses using representative survey data are, however, needed to substantiate the observed qualitative patterns and to further understand the trajectories of farm size expansion and the implications for agricultural productivity and commercialization.