Agriculture is a major consumer of freshwater and is often associated with low water productivity. To prevent drought, farmers tend to over-irrigate, putting a strain on the ever-depleting groundwater resources. To improve modern agricultural techniques and conserve water, quick and accurate estimates of soil water content (SWC) should be made, and irrigation timed correctly in order to optimize crop yield and water use. In this study, soil samples common to the Maltese Islands having different clay, sand, and silt contents were, primarily, investigated to: (a) deduce whether the dielectric constant can be considered as a viable indicator of the SWC for the soils of Malta; (b) determine how soil compaction affects the dielectric constant measurements; and (c) to create calibration curves to directly relate the dielectric constant and the SWC for two different soil types of low and high density. The measurements, which were carried out in the X-band, were facilitated by an experimental setup comprising a two-port Vector Network Analyzer (VNA) connected to a rectangular waveguide system. From data analysis, it was found that for each soil investigated, the dielectric constant increases notably with an increase in both density and SWC. Our findings are expected to aid in future numerical analysis and simulations aimed at developing low-cost, minimally invasive Microwave (MW) systems for localized SWC sensing, and hence, in agricultural water conservation. However, it should be noted that a statistically significant relationship between soil texture and the dielectric constant could not be determined at this stage.