Surface functionalization of hydrolyzed methyl-silsesquioxane films were performed by treatment of samples with trimethylchlorosilane (TMCS) and methyltrichlorosilane (MTCS) dissolved in supercritical carbon dioxide. Films thicknesses modifications, pore size distributions, hydrophobicity, dielectric constants, and chemical reaction analyses were performed by ellipsometry, ellipsometric porosimetry, goniometry, electrical measurements, and Fourier transform infrared spectroscopy, respectively. As results, the properties of the functionalized films were able to be modified in function of reaction conditions (concentration, temperature, and/or pressure). Layers thicker than a monolayer were deposited by both TMCS and MTCS, and a tradeoff between the surface functionalization and layer thickness for both chemicals was observed. The results led to the conclusion that a combination of reagents or processing steps could be used for surface properties tuning.