This study presents the preliminary outcomes of a methodology for the physical and mechanical characterization of various chestnut elements in different states of preservation. Strategizing conservation and retrofit interventions for timber is necessary, and to do this, it is necessary to establish an estimation of physical (transmissivity, thermal conductivity, humidity level, etc.) and mechanical properties (density, compressive or bending strength, etc.). This essential information is typically associated with timber defects, but there are lack of correlations. The primary objective is to establish correlations between thermal and density properties with the aim of preserving original assets. The investigation delves into the relationship between timber density and thermal properties through experimental non-destructive testing (NDT). Two NDTs were employed with the aim of correlating: penetrometric testing and active thermography investigations. The parametric study on the excitation period yielded valuable insights into the temporal dynamics of heat transfer within the timber, underscoring the significance of selecting appropriate excitation periods to capture precise thermal properties. Tabular data on relative humidity for salified, dried, and new samples provided a quantitative backdrop to these observations, unveiling the nuanced effects of humidity on the timber’s thermal response. The results of this study are positioned to inform future conservation efforts by laying the groundwork for a comprehensive understanding of timber’s mechanical properties. Particularly, the challenge lies in accurately estimating density, where surface tests are often less reliable than in-depth ones. Therefore, it is crucial to seek validation through other NDT tests, such as thermographic analysis and visual inspection, and hygrometric tests recognizing their importance in enhancing the reliability of density assessments. This approach will contribute to the development of more discerning preservation strategies.