The management of moisture is one of the main challenges in anticipating and averting food decay and food losses during postharvest processing and storage. Hence, it is imperative to reduce the moisture of freshly harvested products to safe-storage limits in order to inhibit the occurrence of diverse biochemical, microbiological and other moisture-related deteriorative reactions which can contribute to quality degradation. A viable alternative to conventional hot-air drying is the application of low temperatures for drying, which has scarcely been investigated. In this regard, experimental-based modeling is a requisite to gain insights into drying processes. Thus, this study focused on investigating the drying kinetics of wheat (Triticum aestivum L.) cv. ‘Pionier’ under a coherent set of drying air temperatures (T = 10–50 °C), relative humidity (RH = 20–60%), and airflow velocity (v = 0.15–1.00 ms−1). A robust and automated measurement system using a high precision balance was utilized as a basis for the real-time and continuous acquisition of drying data. The analysis of the experimental results facilitated the establishment of generalized drying model for low temperatures able to describe at a high accuracy the behavior of moisture ratio X* (R2 = 0.997, RMSE = 1.285 × 10−2, MAPE = 6.5%). An analytical model for predicting the effective diffusion coefficients D (R2 = 0.988, RMSE = 4.239 × 10−2, MAPE = 7.7%) was also developed. In conclusion, the anticipated drying model has demonstrated the capability of modeling the drying behavior of wheat at low temperatures with a high temporal resolution and should be employed in the design, analysis and modeling of cooling, aeration and low-temperature drying processes of wheat bulks.