Wondering if this is VERY rare & possibly valueable or worthless and insignifigant. I can barely find more than a couple of mentions anywhere online about it or even pictures.

It's a Sony Walkman 1985 Special Edition made to celebrate 25 Years in America for Sony. The model is WM - 11/22

Anyone know much about this and it's rareity? Thanks in advance

WM-11/22's don't go for much but are still nice enough IMO. Although we don't tend to value stuff as such here at S2G, this I would say is quite sellable particularly if boxed with heaphones etc. Best bet is to do a completed items search on eBay...

Well well I certainly have never heard of seen of the US Anniversary model.  Although as Nak D said this model is not hard to find and not a expensive model when new that it is a Market specific Anniversary model which I dont know many such as the WM-WE01 for Japanese Market only as 20th anniversary it certainly ups the value.  Not been buying much Walkman in past year so personally bit out of touch with values currently.