Nanotechnology comprises a promising approach towards the update of dental materials.The present study focuses on the reinforcement ofdental nanocomposite resins with diverse organomodified montmorillonite (OMMT) nanofillers. The aim is to investigate whether the presence of functional groups in the chemical structure of the nanoclay organic modifier may virtually influence the physicochemical and/or the mechanical attitude of the dental resin nanocomposites. The structure and morphology of the prepared materials were investigated by means of wide angle X-ray diffraction and scanning electron microscopy analysis. Fourier transform infrared spectroscopy was used to determine the variation of the degree of conversion over time. Measurements of polymerization shrinkage and mechanical properties were conducted with a linear variable displacement transducer apparatus and a dynamometer, respectively. All the obtained nanocomposites revealed intercalated structures and most of them had an extensive filler distribution into the polymer matrix. Polymerization kinetics werefound to be influenced by the variance of the clay organomodifier, whilenanoclays with vinyl groups considerably increased the degree of conversion. Polymerization shrinkage was almost limited up to 50% by incorporating nanoclays. The absence of reactive groups in the OMMT structure may retain setting contraction atlow levels. An enhancement of the flexural modulus was observed, mainly by using clay nanoparticles decorated with methacrylated groups, along with a decrease in the flexural strength at a high filler loading. The overall best performance was found for the nanocomposites with OMMTs containing double bonds. The significance of the current work relies on providing novel information about chemical interactions phenomena between nanofillers and the organic matrix towards the improvement of dental restorative materials.