The use of fluorescence and colorimetric chemosensors to detect chiral molecules has been a central focus of recent efforts in the field of sensor technologies, owing to the fact that enantiomerically pure compounds and drugs have unparalleled importance in bioscience, clinical medicine, and bionics areas. The most involved chiral recognition mechanism with these sensors is based on hydrogen bond interaction that is employed successfully in organic solvents. This confines these sensors to be used for the water-soluble chiral analyte detections and the chiral recognition applications in physiological environment. The development of the chiral sensors that can be used efficiently in aqueous solutions, such as boronic acid-based sensors or electrostatic sensing systems, should be the focused task in this area. The polymer-based sensors have the capacities to amplify the chiral recognition signal further enhancing the sensitivity and the enantioselectivity. Those macrocyclic scaffolds can utilize their rigid structures to improve the enantioselectivity in the chiral recognition process.