In recent years, π-conjugated liquid crystalline molecules with optoelectronic functionalities have garnered considerable attention, and integrating these molecules into side-chain liquid crystalline polymers (SCLCPs) holds potential for developing devices that are operational near room temperature. However, it is difficult to design SCLCPs with excellent processability because liquid crystalline mesogens are rigid rods, have low solubility in organic solvents, and have a high isotropization temperature. Recently, we developed near-room-temperature π-conjugated nematic liquid crystals based on “bridged stilbene”. In this work, we synthesized a polyacrylate SCLCP incorporating a bridged stilbene that exhibited a nematic phase near room temperature and could maintain liquid crystallinity for more than three months. We conducted a thorough phase structure analysis and evaluated the optical properties. The birefringence values of the resulting polymers were higher than those of the corresponding monomers because of the enhanced order parameters due to the polymer effect. In addition, the synthesized polymers inherited mesogen-derived AIE properties, with high quantum yields (Φfl = 0.14–0.35) in the solid state. It is noteworthy that the maximum fluorescence wavelength exhibited a redshift of greater than 27 nm as a consequence of film formation. Thus, several unique characteristics of the SCLCPs are unattainable with small molecular systems.