Wood protection through chemical modification has received increasing interest over the last decades due to the environmental issues related to conventional biocides or protecting products. Consequently, a wide range of new treatments are developed in laboratories, which are later scaled up in the industrial environment. The main goal of modifying wood for indoor–outdoor application is to change its hydrophilic character, which in turn improves the intrinsic properties of the material and its durability against external factors. Wood can be esterified through its hydroxyl groups to obtain a hydrophobic and photo-stable material. Chemical modifications of Pinus radiata D. Don wood using hexanoyl chloride (P6), dodecanoyl chloride (P12), and stearoyl chloride (P18) were carried out at different concentrations. Esterification was confirmed by Fourier Transform Infrared Spectroscopy (FTIR) technique combined with a discriminatory analysis. Weight percent gain was associated with the number of carbons of the aliphatic chain of the fatty acid (P6 > P12 > P18). Moreover, an increase of wood density as a consequence of modification treatments was observed. A substantial improvement of the hydrophobicity of wood was observed by dynamic contact angle measurements. In addition, the effect of ultraviolet (UV) radiation on color changes was reduced with the treatments. Furthermore, the P6 treatment presented acceptable values of modulus of elasticity (MOE) and modulus of rupture (MOR), being suitable for similar mechanical uses as non-treated pinewood. However, only treatments P12 and P18 enhanced thermal resistance of the pinewood in an oxidative atmosphere.