The fretless is likely from Buckbee's factory. 1880-1920?
The fretted one looks entirely homemade, except for the hardware. Could have been made almost any time during the 20th c., or the last couple decades of the 19th. Some of its features (like no heel on the neck) give it an archaic look, but the overall proportions suggest to me the influence of designs from at earliest the 19-teens. A very rough guess.
From what I can see in the pictures, the hooks, shoes, and nuts match (mostly). If that's the case, they're probably original to the instrument. Share some close-ups, and there's probably someone here who will be able to tell you when those particular patterns were first made, giving you an idea of the earliest possible date on the banjo.