The Salcheto winery has undertaken a process of reduction of its primary energy consumption and the implementation of green energy technologies. They adopted solar photovoltaic, wood biomass, and geothermal energy sources. A horizontal ground source heat exchanger (GSHE) plant is used to cool a part of the pressed grapes and control the wine production temperature. The goal of this work was to investigate some technical issues of the plant and to increase the efficiency of the whole system. The first step was the evaluation of the actual operating conditions of the GSHE plant, by performing a thermal response test. The results allowed us to find the thermal diffusivity of 3.5 × 10−7 m2/s, and the calculation with the IGSHPA standard indicated a cooling performance of about 6 kW. A survey during the harvest highlighted a peak power of 6 kW. Therefore, to improve the plant, some modifications were proposed and analyzed. In the new layout, the geothermal plant serves the condenser of the refrigeration unit, allowing cooling of the all production lines, instead of only one. The peak power was evaluated as 32 kW, and the GSHE can fulfil this, up to 18 kW. For higher power, the evaporative tower will supply the remainder, covering a maximum of 45%. Furthermore, the refrigeration unit may cover the cooling requirements of the entire residential and office building, without other plant improvements.