I purchased a small lot of pocket watches at a flea market in Myrtle Beach recently. The lot contained these three Waltham pieces. None of the watches were running. I was able to open up one of the Waltham watches and the movement looked to be in pristine shape. I sent the three Waltham pocket watches to my watchmaker here in Korea to have the movements serviced. I'm hoping to learn more from him. At least he can tell me the serial numbers so I can look up the dates on these.
I'll update when I get them back from the watchmaker!
If I had to guess, I'd say the Waltham with the off-white (dirty) dial dates from the 1930s. As to the first image, the watch with roman numerals, I'm really hoping that predates 1900.