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Depends. My mom got one used not long ago, a little single shot, and she paid $200. But there are some lever action .22s for sale at the local gunshop that are over $900 a piece. So it depends on what type of Winchester, really.
 

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disappointed & disgusted, But DETERMINED...
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OP if you can find one, great. Jump on it. The newer ones aren't worth the $ you'd spend on one of an older vintage.


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It is not all that uncommon for some nice Win 22's to sell for well above $500 and even above $1000. But like any kind of collector item you have to know exactly what it is.
 

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...And if you're patient you can find one mechanically sound and cosmetically challenged like this Model 1906 I found recently for under $350.00 which had no rust, but the bluing has thinned to a brown/grey patina, perfect mirror bore, with the wood bespeckled with 100 years of dings and dangs, but no cracks. Shoots and functions like a champ. Won't win any beauty contests, but remains a contender for a friendly competition to see who buys lunch...

I wanted one because I, well... wanted one.

 

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The answer is similar to the answer to "Are Ford cars expensive?" Answer- Depends. Do you mean a 12 year old Ford Taurus, or a Shelby Cobra?

There are some classic Winchester Mdl 52s nearing their 100th birthday that will cost your first born child. And there is a a Model 190 that is well worn, and is a $100 squirrel shooter.

With ANY firearm, Make, Model, Condition- all 3 factors will drive the value. The exception is a gun connected to a historical figure WITH the paperwork to prove the connection (known as provenance).
 
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