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An "antique" flour mill my grandfather built sold for $80ish and that had to be a local auction since shipping would have been impossible. (Keep in mind we didn't even know what this was until we saw the grain in the cracks.)

A 60s vacuum that didn't sell for $5 at my garage sale sold for $250 (+$40 shipping) (Good thing it didn't sell at the garage sale.)

An old pamplet from NSP (the local gas company) sold for $14.

I picked up 30 or so "Orbitz" soda when my dollar storee was clearing them out for a quarter. They've fetched as much as $15. The scarier thing was when the boxes sold too!