In order to realize a smart nano-machining and measurement system based on atomic force microscope (AFM), we have been developing diamond probes with a high-aspect-ratio, sharpened diamond tip. In this paper, we described the most important micromachining techniques for the fabrication of the diamond probes. The high-aspect-ratio diamond microstructures were successfully fabricated by employing our proposed two-step reactive ion etching (RIE) processes. A novel bonding technique of diamond to Si at wafer level was also developed by using an inorganic-organic hybrid sol-gel film (MeSiO3/2) as an adhesive layer to prepare a diamond/SOI wafer as the starting material. Moreover, we demonstrated the applicability of a fabricated diamond probe not only to AFM measurements but also to a tool for nanomachining.