According to Forbes, the median annual property tax in the Bestchester is a whopping $8,404. That's over six times the national average. Why do people put up with it? Having grown up there, I'm not entirely sure. But proximity to Bill and Hillary Clinton (on the rare occasion when they're actually cooped up in their Chappaqua abode), the lack of reality TV crews in the area and the chance to party in nightlife mecca White Plains don't hurt. (The real reason is "village autonomy," which means property taxes make up for a lack of statewide levies and industrial bases in residential pockets.)
Rounding out the top five were horsey Hunterdon (New Jersey); trafficked Nassau (Long Island); hellish, table-throwing Bergen (also Jersey); and boondocks Rockland (New York, but upstate). Rockland's median number of $7,798 might have placed it fifth in the area, but it's closest competitor when taking the rest of America into consideration was Lake County (Illinois) at a lowly $6,052.