All depends on what you want or need. I already own a 27-2 5" so personaly I would go for the winchester. The rifle should be worth more now and later. I am surprised that in like good condition that they are in the same price range. The winchester would be bought to collect and not shoot, the 27 would be bought to use.
I just know this is going to po some here. I bought my 27-2 NIB around 1970. I sent it back to smith, got all the options put on. Presentation smooth grips, red insert, wo rear sight, target hammer and trigger plus my name engraved in a gold oval on the side plate and the wood case. I shot it a little initaly, maybe requalfied with it for my job on a half dozzen requals or so. Other than that its been a safe queen for 40 years! Why? Because I have owned and still own other 357s that are lighter, therefore handyier and easier to pack that are just as accurate. Colt troopers, a 66-3, 2 1/2" python etc. I also own a companion 5" 29-2. I have come to find through the years that if I carry a N frame for the day on rideing the trails ATVing, I prefer a .44 special 24-3 4" that is lighter or a old converted HD to .44 special.
Now I have to get that jewel out of the safe and see what it looks like!