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(1) Background: The objective of this study was to develop a novel dental nanocomposite containing dimethylaminohexadecyl methacrylate (DMAHDM), 2-methacryloyloxyethyl phosphorylcholine (MPC), and nanoparticles of calcium fluoride (nCaF₂) for preventing recurrent caries via antibacterial, protein repellent and fluoride releasing capabilities. (2) Methods: Composites were made by adding 3% MPC, 3% DMAHDM and 15% nCaF₂ into bisphenol A glycidyl dimethacrylate (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) (denoted BT). Calcium and fluoride ion releases were evaluated. Biofilms of human saliva were assessed. (3) Results: nCaF₂+DMAHDM+MPC composite had the lowest biofilm colony forming units (CFU) and the greatest ion release; however, its mechanical properties were lower than commercial control composite (<i>p</i> < 0.05). nCaF₂+DMAHDM composite had similarly potent biofilm reduction, with mechanical properties matching commercial control composite (<i>p</i> > 0.05). Fluoride and calcium ion releases from nCaF₂+DMAHDM were much more than commercial composite. Biofilm CFU on composite was reduced by 4 logs (<i>n</i> = 9, <i>p</i> < 0.05). Biofilm metabolic activity and lactic acid were also substantially reduced by nCaF₂+DMAHDM, compared to commercial control composite (<i>p</i> < 0.05). (4) Conclusions: The novel nanocomposite nCaF₂+DMAHDM achieved strong antibacterial and ion release capabilities, without compromising the mechanical properties. This bioactive nanocomposite is promising to reduce biofilm acid production, inhibit recurrent caries, and increase restoration longevity.