When it comes to old Winchesters it's all about the year manufactured, the rarity of the particular model or sub model and the condition they are in. Just because it's a "Model" 1897 or 1890 doesn't mean they were built then. The Model designation generally is the year of first production and most of them ran through the turn of the century and into the early 1900's. Go to the Winchester web sight and you can find the age of your guns by inputing the serial numbers. The earlier (1800's) the more expensive the guns will be. There are of course other factors involved as some sub models are rarer than others etc...
I love old Winchesters too!
Model 1892 (built in 1897)
Model 1890 (built in 1894)
Model 1887 (Built in 1888)
Model 1873 (Built in 1883)
Model 1866 "Yellow Boy" (Built in 1868)