Objective: To evaluate and compare the surface roughness and gloss of a DMA-free composite and Bis-GMA-free composite with a DMA-based composite before and after toothbrushing simulation. Materials and Methods: Fifteen dimensionally standardised composite specimens of three nano-hybrid resin composites (Tetric EvoCeram, Admira Fusion, and Venus Diamond) were used. Five specimens from each composite were polished and then subjected to a toothbrushing simulator. Surface roughness (Ra) and gloss were measured before toothbrushing and after 5000, 10,000, 15,000, and 20,000 toothbrushing cycles. The data was analysed using 5 × 3 ANOVA to assess surface roughness and gloss values and pairwise comparisons in the form of Tukey post hoc tests were performed to interpret main effects. Results: For all tested materials, surface roughness increased, and gloss decreased after toothbrushing abrasion. Surface roughness (Ra) values ranged from 0.14 to 0.22 μm at baseline and increased to between 0.41 and 0.49 μm after 20,000 toothbrushing cycles. Gloss values ranged between 31.9 and 50.6 GU at baseline and between 5.1 and 19.5 GU after 20,000 toothbrushing cycles. The lowest initial Ra value was detected in Venus Diamond and the highest initial gloss value was detected in Tetric EvoCeram. Conclusions: Simulated toothbrushing abrasion led to an increase in surface roughness and a decrease in gloss for all tested materials. Venus Diamond had the smoothest surface and Tetric EvoCeram had the glossiest surface after polishing and following 20,000 cycles of toothbrushing abrasion. Admira Fusion demonstrated the roughest surface and had the lowest gloss values before and after toothbrushing abrasion.