Agriculture is the mainstay of economic activities in the Western Cape Province, South Africa. The government took various initiatives to boost the involvement and participation of previously disadvantaged people in agriculture post-apartheid and colonial eras. However, ownership of land and agricultural productivity, by blacks, have faced consistent challenges. This paper uses the critical success factors of black-owned commercial farm real estate niche in the Western Cape to examine the farming experiences of blacks in the Western Cape Province. The critical success factors identified in the study include farm land, capital, expertise, human resource management, involvement in the value chain and cultivars. Access to funding and water are also vital to successful farming. A black farmer should balance these factors appropriately to avoid the pitfalls that often confront inexperienced and under-privileged farmers.