Rory, certainly not an expert, but I’ve had 10-15 wooden Winchester ammo boxes over the years (still have a bunch). The oldest wooden boxes are dovetailed. Not based on anything, but I’d say your box with the nails is post war. Prices are all over the place depending upon condition and what caliber ammo they held and as always how badly someone wants one. $50.00 - $75.00, but have seen them go for double that on the auction sites.
There are a lot more Shotshell boxes.
