Robotic and/or measurement devices, systems, and methods for telesurgical and other applications employ input devices operatively coupled to tools so as to allow a system user to manipulate tissues and other structures being measured. The system may make use of three dimensional position information from stereoscopic images. Two or more discrete points can be designated in three dimensions so as to provide a cumulative length along a straight or curving structure, an area measurement, a volume measurement, or the like. The discrete points may be identified by a single surgical tool or by distances separating two or more surgical tools, with the user optionally measuring a structure longer than a field of view of the stereoscopic image capture device by walking a pair of tools “hand-over-hand” along the structure. By allowing the system user to interact with the tissues while designating the tissue locations, and by employing imaging data to determine the measurements, the measurement accuracy and ease of measurement may be enhanced.