I give questions like these allot of thought, as I let a few family guns go about 15 years ago and still question whether or not I should have. On rare occasions where I'm really honest with myself, there is a bit of a lingering regret about it. However, I also ask myself whether or not I would have EVER shot them between then and now, and the answer is "no". It also comforts me knowing how pragmatic that (deceased) family member was, I can't see him ever holding onto guns he never used, they would have likely been moved down the road FOR something he could have put to use.
I know ^that wasn't the question, but something to consider (maybe?) when selling family guns. Something as old as your Winchester, with perhaps modest resale value, that is chambered in a caliber you can still buy off the shelf=I'd probably keep it.