The rapid advancement of the miniaturization techniques for high-frequency transceivers, radars, and communication systems operating in the D-band (110–170 GHz) has positioned circular dielectric waveguides (CDWGs) as a promising transmission-line alternative. Yet, their potential has not been fully exploited. This work fills this gap by introducing novel, compact CDWG-fed lens antenna solutions that deliver excellent gain and impedance matching performance. A low-loss, low-cost, and flexible CDWG made of low-density polyethylene is used to excite dielectric lens antennas of various sizes, contours, and materials, enabling a systematic evaluation of the impact of lens geometry on antenna performance. Through detailed electromagnetic simulations and experimental validations, lenses of different sizes and contours are designed. The proposed CDWG-lens configuration achieves measured broadband matching better than 17 dB and stable high gain across 115–130 GHz. Measured gains of 21–23 dBi for lenses with diameter of 10.6 mm and gain factor of 27–28 dBi for lenses with diameter of 20 mm confirm the high aperture efficiency and novelty of this approach. A strong agreement between the simulation and the measurement results is also observed. These compact and efficient lens antennas combined with the advantages of CDWG feed, can be integrated as a part of advanced system applications in the D-band frequency range like radar sensing and communications.