Squeezing the quadrature noise of a harmonic oscillator used as a sensor can enhance its sensitivity in certain measurment schemes. The canonical approach, based on parametric modulation of the oscillation frequency, is usually limited to a squeezing of at most 3 dB. However, this can be overcome by additional stabilization of the anti-squeezed quadrature. Here, we apply this approach to highly-stressed silicon nitride membrane resonators, with effective masses of the order few nanograms and quality factors routinely exceeding 108, which hold promise for sensing applications in both the classical and quantum regimes. We benchmark their performance using either piezo or capacitive parametric modulation. We observe maximum thermomechanical squeezing by record-high 17 dB and 21 dB, respectively, and we argue that even larger values can be attained with minimal changes to the device design. Finally, we provide a full quantum theory of a combination of this approach with quantum-limited motion measurement and conclude that quantum squeezing is attainable at moderate cryogenic temperatures.