The financial impact of implementing tree-based windbreaks in South African mandarin orchards was investigated based on a case study from the Western Cape. Windbreaks protect fruit quality and prevent windfall during strong winds but come with establishment costs and land sacrifices to avoid competition with fruit crops. The financial value of windbreaks was assessed using stochastic discounted cash flow techniques. The results show that tree-based systems and agricultural nets outperform open fields in terms of net present value (NPV) and annualized gross margin (AGM). The best windbreak design achieves a mean per-hectare NPV of USD 99,243 over 20 years, while nets have a higher NPV of USD 117,519 and AGM of USD 15,795. Windbreaks also offer shorter discounted payback periods (DPBP) due to reduced orchard costs, while open fields are riskier due to wind damage. Farmers’ decisions may be influenced by the internal rate of return (IRR) and DPBP, with nets having a higher NPV but lower IRR compared to windbreaks. Windbreaks offer indirect benefits, like biodiversity enhancement and climate change mitigation, but data limitations prevent further analysis. More research is needed to quantify the broader ecosystem services of windbreaks and their valuation.