Rotatable, oblique-viewing stereoendoscope including a dual-pupil aperture divided to a first pupil and a second pupil, a proximal objective assembly positioned proximally to the dual-pupil aperture, a first image sensor configured to detect a first image focused by the proximal objective assembly and a second image sensor configured to detect a second image focused by the proximal objective assembly, a relay system positioned distally to the dual-pupil aperture and a front optical system positioned distally to the relay system, the front optical system including a folding prism, wherein the front optical system is configured to reimage the dual-pupil aperture at a distal end thereof, thereby producing an image of the first pupil and an image of the second pupil at a distal pupil plane and wherein the stereoendoscope does not include a negative power lens positioned distally to the folding prism.