Measuring the soil water content (SWC) is a fundamental component of the sustainable management of water resources, soil preservation, and high irrigation efficiency. Non-destructive SWC measurements using soil moisture sensors (SMSs) enables timely irrigation and reduces overirrigation and water stress. Within this context, the performance of four commercial single-point soil moisture sensors (Watermark and tensiometer (Irrometer Company, Inc., Riverside, CA, USA), SM150 (Delta-T Devices, Cambridge, UK)), FieldScout TDR300 (Spectrum Technologies, Aurora, IL, USA) and one soil profile PR2 probe (Delta-T Devices, Cambridge, UK) were tested under anthropogenic eutric cambisol with a silty clay loamy texture (20, 30, and 40 cm) to evaluate accuracy and sensitivity to changes in the SWC in an irrigated apple orchard. The Watermark and tensiometer were additionally tested in the laboratory to convert soil water tension (kPa) to the volumetric soil water content (%vol.). In general, all tested SMSs responded to changes in the SWC, with sensor-to-sensor differences. The Watermark and tensiometer underestimated the SWC, while the TDR overestimated the SWC. The SM150 and PR2 showed high accuracy, i.e., SM150—RMSE-2.24 (20 cm), 2.18 (30 cm) and 2.34 (40 cm), MSE—5.02 (20 cm), 2.93 (30 cm) and 1.89 (40 cm), and PR2—RMSE-1.8 (20 cm), 1.3 (30 cm) and 1.55 (40 cm), MSE-3.23 (20 cm), 1.7 (30 cm) and 2.39 (40 cm) at all observed soil depths.