The development of two-photon lithographic technologies is enabling the fabrication of 3D structures at sub-micron resolution with optical materials. The freedom allotted by these technologies allows for the fabrication of miniaturized optical systems and complex micro-optical components. Additionally, the ability to rapid prototype micro-optical components with these technologies makes it suitable for providing an option for custom tailored imaging applications that include quantitative imaging modalities. Utilizing such technologies, an advanced approach is taken for the development of a fiberscope for specific imaging applications. Sub-millimeter freeform shape lenses, aperture, and micro-optical housing are fabricated as distal-end components to replace conventional micro-optical components of an endoscopic platform to enable long-working distance, high-resolution, imaging applications. Beam shapers are also fabricated at the distal ends of optical fibers to reduce the numerical aperture of each illumination fiber, aligning the area of illumination to the area observed by the imager. Optimization of beam shapers serves to provide relatively uniform and non-saturated illumination of the target area. Together, this custom optical system can outperform commercially available equivalents and is an example of how this 3D fabrication technology can offer improved alternatives to conventional micro-optics of today. Moving forward, development and incorporation of more complex micro-optical components, such as diffractive optical elements together with additional 3D printed sensors, can serve to bring quantitative power to further expanding the applicability of new miniaturized imaging and sensing systems. Examples to illustrate capabilities are presented.