Wish I could see the butt. Let's assume some scratches. I'm actually quite stumped about what grade it is. Winchester seems to make Featherweight, Sporter and Super Grade. They also makes some "special" grade guns each year. With forend capped/lined, gloss finish, and the jeweled bolt, I'm thinking super grade or some "special". Supergrade marked as such on the triggerguard.
I think mid to later 2000's is the right timeframe. I have one from that timeframe that was very well made, IMO.
In great condition, I think it would retail in the $1000 range. I would reduce by $400 for stock damage based on your description, not on what I see in pics. It looks slightly better in those pics. Then I would add $200 for a Leupold Golden Ring scope. So, $800 retail price in the "gun room" at Cabelas.
I think you could sell to a a Winchester 70 shooter looking for a new rifle for $700. $550ish to somebody less interested. Selling to a retail store will generally net you 50% of full retail price....like $400.
i might be overvaluing the scope by $50, depending on its age. I'm almost guessing at the condition, since the most important part, butt & grip not shown.