I would sell off three and keep one like you are planning. I would think you could get a good price for them right now with the demad so high.
In the last year or so I sold off all my Gen 1 & 2 Glocks complete with the NDF pre ban mags I had. Used Gunbroker. I got premium $ (relative to used Glocks) and I recollect that every one went to a buyer or dealer in MA. I love the Gen 5's so no loss to me. If those 4 came to be mine I would do it again.
If they are manufactured prior to the 1994 Clinton Crime Bill making them Pre-Ban in the eyes of CT buyers. People look for pre-ban pistols which are the only way to legally suppress in CT.
Honestly, Glocks are Glocks. If you want to keep around an old one for historical purposes that's cool, but I would definitely flip the other 3. If you're selling to a gun store and they're bone stock with 2 mags I'd expect anywhere from $350-$400, probably closer to $350.
Thanks for the input everyone. The four G19s are on their way to a consignment sale at:
https://fsguns.com/
The good folks in MA get some pistols, I get $100-150 each more than if I sell locally assuming they sell and The Four Seasons folks keep their end of the bargain and send me a check.
I really appreciate all the input. I did not know of the need for Gen 2 pistols in MA.
Another update:
My G19s arrived at https://fsguns.com/ in MA. They are consignment items. At the price they are asking for them I may end up with $650/pistol. This is entirely shocking to me. The folks at the shop have been great to deal with so far and they say G19s don't last long at all. We'll see if they sell...
So thank you much to our MA members, I owe you guys a lunch or something if you ever visit free Arizona.
Also: If you have Gen 2 G19s to get rid of: Send them to Massachusetts and you may double your money.
I bought two NIB Gen 2 G19s from Don Streicher's Police Supply in 1989, my first Glocks ever.
He kindly gave them to me for the LE price even though I wasn't LE.
Gave one of them as a gift to my then wife-to-be in 1993 when she (smart girl!) evinced an interest in owning a firearm.
Had the slides hard chromed after they began to get pretty worn, maybe twenty years ago.
Had the prescribed Glock factory upgrades, and later got Heinie sights.
Nary a malfunction after break in. I still have the original four non-metal-lined magazines (some with witness-hole cracks), booklets, brushes and boxes.
Nowadays they run with modern OEM magazines, otherwise they're stock except for Wolff springs and guide rods plus Glock 3.5# connectors, OEM extended slidestop levers, and Striker Control Devices. (Some day I'll replace those Wolff parts with current OEM RSAs.)
No frame cracks, undue wear or any other problems even after 30+ years.
I never intend to sell them.
"Therefore, since the world has still... Much good, but much less good than ill,
And while the sun and moon endure, Luck's a chance, but trouble's sure,
I'd face it as a wise man would, And train for ill and not for good." -- A.E. Housman