Beanie Babies
I guess teddy bears and their variations never quite go out of circulation and popularity. Beanie Babies bloomed in the early 1990’s and then declined in the late 2000’s, but not everyone stopped caring for them. Some collectors are willing to pay thousands for some types of Beanie Babies. One example is the 1997 1st Edition Princess Diana Beanie Bear which can go for $12,000.
Lionel’s Pennsylvania “Trail Blazer” Train Set
It might not have been yours, but there’s still a chance you have it lying around. The 1934 Standard Gauge version of this train can get you something like $250,000. It’s worth looking in the attic again.