We report the discovery of three transiting low-mass companions to aged stars: a brown dwarf (TOI-2336b) and two objects near the hydrogen burning mass limit (TOI-1608b and TOI-2521b). These three systems were first identified using data from the Transiting Exoplanet Survey Satellite (TESS). TOI-2336b has a radius of 1.05 ± 0.04 RJ, a mass of 69.9 ± 2.3 MJ and an orbital period of 7.71 d. TOI-1608b has a radius of 1.21 ± 0.06 RJ, a mass of 90.7 ± 3.7 MJ and an orbital period of 2.47 d. TOI-2521b has a radius of 1.01 ± 0.04 RJ, a mass of 77.5 ± 3.3 MJ, and an orbital period of 5.56 d. We found all these low-mass companions are inflated. We fitted a relation between radius, mass, and incident flux using the sample of known transiting brown dwarfs and low-mass M dwarfs. We found a positive correlation between the flux and the radius for brown dwarfs and for low-mass stars that is weaker than the correlation observed for giant planets. We also found that TOI-1608 and TOI-2521 are very likely to be spin-orbit synchronized, leading to the unusually rapid rotation of the primary stars considering their evolutionary stages. Our estimates indicate that both systems have much shorter spin-orbit synchronization time-scales compared to their ages. These systems provide valuable insights into the evolution of stellar systems with brown dwarf and low-mass stellar companions influenced by tidal effects.