In this research, we focused on Human-Robot collaboration. There were two goals: (1) to develop and evaluate a real-time Human-Robot collaborative system, and (2) to achieve concrete tasks such as collaborative peg-in-hole using the developed system. We proposed an algorithm for visual sensing and robot hand control to perform collaborative motion, and we analyzed the stability of the collaborative system and a so-called collaborative error caused by image processing and latency. We achieved collaborative motion using this developed system and evaluated the collaborative error on the basis of the analysis results. Moreover, we aimed to realize a collaborative peg-in-hole task that required a system with high speed and high accuracy. To achieve this goal, we analyzed the conditions required for performing the collaborative peg-in-hole task from the viewpoints of geometric, force and posture conditions. Finally, in this work, we show the experimental results and data of the collaborative peg-in-hole task, and we examine the effectiveness of our collaborative system.