Optical coherence tomography (OCT) allows for non-contact, high resolution, volumetric imaging of biological tissue and has become an indispensable ophthalmic imaging technique. However, conventional, commercial OCT systems require a cooperative, sitting patient typically stabilized by a head and/or chin rests. Additionally, current clinical systems are designed for imaging either the anterior or posterior segment of the eye exclusively. While these limitations are not severe in the ophthalmic clinic, they do limit the use of OCT in other more challenging medical environments where novel “whole eye” imaging could provide value, such as in the military theater or emergency department (ED). One solution to eliminate the need for a patient to sit upright and be stabilized during imaging would be a hand-held probe positioned and stabilized by the photographer or physician. Here we describe a hand-held OCT probe for simultaneous imaging of the anterior chamber (13.3 mm diameter field-of-view) and posterior segment (40° as measured from the pupil nodal point) simultaneously. The use of polarization multiplexing allows for two independent imaging channels which enable a wide posterior segment field-of-view and the ability to control the posterior segment path length and focal depth independently from the anterior chamber channel. Additionally, the probe was designed for a relatively compact form factor.