The Winchester 416 is a re-badging of the Diana-made model 16. This gun, and the similar model 15 which had only a simple wood butt instead of a full stock, were made from the early 1950's up until the early 80's. The Winchester-labeled guns were made around 1969 to 75. Very similar guns were made by Diana for many years before WW2, and by Milbro in Scotland (made on pre-war German machinery) after the war.
It's very well-made and finished, but still is regarded as a kid's gun, was made in relatively large numbers, and is not too valuable. A truly mint one might bring $100 (strictly my opinion), maybe a bit more with the Winchester label or with original packaging, etc. Less money for lesser condition.