With an expenditure of 111 billion dollars a year, the field of dentistry needs a new methodology for repairing patients’ teeth. The current techniques and procedures to repair teeth could be considered temporary or expensive procedures. The need has risen to develop a new procedure that can regenerate human teeth and repair the damaged area. This investigation explores the possibility of creating a new methodology to regenerate a patient’s damaged and decaying teeth. This research investigates infusing calcium-hydroxyapatite (C-HAp) and gentamicin into electrospun nanofibers, thus creating a non-woven nanofibrous tissue, which is then amalgamated with a 50/50 solution of polycaprolactone (PCL). The nanofibrous tissues were prepared and characterized by means of a scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FTIR), and Roman spectroscopy for porosity, cell adhesion capability, and chemical composition. Biocompatibility and anti-bacterial tests were done to check the viability of the material to be used to help propagate the regeneration of damaged dentin material in human teeth. It was seen that the sample tissues had properties to help kill Streptococcus mutans, which is the leading bacteria that causes tooth decay. The mechanotransduction of bone modeling shows that the ability of the body to regenerate bone mass and density could be possible under the correct environment. The new methodology will address environmental concerns of the human anatomy and help the natural healing cycle of the damaged areas of the tooth. The samples were tested for cytotoxicity by means of cell culturing and MTT assay. The tissue characteristics show an extensive nanofiber structure infused with C-HAp, antibiotics and PCL for regeneration of the tooth dentin. This research investigation has great potential for a new methodology in the dental field to help the populace maintain a better way of life at a cheaper cost, over time.