Motivated by the interpretation of the recent results on the TeV gamma radiation from the Galactic center, including the new 2004 HESS data, as a by-product of dark matter particles annihilations, we address the question of the largest possible neutralino masses and pair annihilation cross sections in supersymmetric models. Extending the parameter space of minimal models, such as the mSUGRA and the mAMSB scenarios, to general soft SUSY breaking Higgs masses gives access to the largest possible pair annihilation rates, corresponding to resonantly annihilating neutralinos with maximal gaugino-higgsino mixing. Adopting a model-independent approach, we provide analytical and numerical upper limits for the neutralino pair annihilation cross section. A possible loophole is given by the occurrence of non-perturbative electro-weak resonances, a case we also consider here. Finally, we outline the ranges of neutralino masses and cross sections for models thermally producing a WMAP relic abundance, thus providing reference values for “best-case” indirect SUSY dark matter detection rates.