A medical observation apparatus includes: an imaging device configured to capture an observation target to obtain a captured right eye medical image and a captured left eye medical image; and circuitry configured to: acquire positions of at least two points in the observation target, the positions being determined based on predetermined operation on the observation target; and cause the captured right eye medical image, the captured left eye medical image, and an annotation image, to be displayed on a display screen of a display device, the annotation image indicating a distance between two points at the acquired positions.