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As rural poverty deepens over much of Sub-Saharan Africa, smallholder transformation has become more urgent than ever before. A majority of rural people derive their livelihoods from agriculture, hence the urgent need for transforming the sector. The South African government launched a comprehensive land reform programme at the dawn of democracy in the country on the assumption that constraints on land size would be eliminated to make room for a more inclusive agricultural economy. The present study sought to assess how cultivated area affects food security and the profits of maize and cabbage farmers. The purposive sampling technique was used for the selection of study sites, from which 158 irrigators and homestead gardeners were selected. The data were then subjected to analysis by defining a maximum likelihood estimator that combines the seemingly unrelated regression (SUR) and one-way error correction model, to determine the factors influencing food security and farm profits. The model revealed diverse relationships, suggesting that location, farm type and income were important variables in explaining food security. The area under cultivation was found to influence profits for both crops. Policies in favour of technology adoption, market access and input use would greatly incentivize farmers to cultivate larger plots of land.