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Utilizing data from the ELVIS and Via Lactea-II simulations, we characterize the local dark matter subhalo population, and use this information to refine the predictions for the gamma-ray fluxes arising from annihilating dark matter in this class of objects. We find that the shapes of nearby subhalos are significantly altered by tidal effects, and are generally not well described by NFW density profiles, instead prefering power-law profiles with an exponential cutoff. From the subhalo candidates detected by the Fermi Gamma-Ray Space Telescope, we place limits on the dark matter annihilation cross section that are only modestly weaker than those based on observations of dwarf galaxies. We also calculate the fraction of observable subhalos that are predicted to be spatially extended at a level potentially discernible to Fermi.