That bike is pretty easy to date to mid 1960s because it has the 8” crank arms, the flatter mud guards, and the older style Raleigh font decals. Do no damage to those crank arms, they only used the 8” version on that bike for 4-5 years, typically with a 46 tooth front sprocket. Very tough to find, today. The more common crank arm is 7 1/2”, typically used with a 44 tooth front sprocket. Customers could choose from a few different back sprockets, if they asked.
The mud guards were changed to a more rounded design around 1970, that was used until the end of production. I have a bike dated December, of 1981, a 24” with the hockey stick chain guard. The very rare 22” men’s bikes usually have a full chain case. I have 4 Roadsters, 3 24” men’s, and a 22” woman’s.
My son rides the identical bike, and used it successfully for this years Lake Pepin 3 speed tour, with a 20 tooth rear sprocket I put there, in difference to the hill at Bay City. I also used a 24” Roadster, but, I converted the AW hub to S5 configuration, in difference to my age, the hills, and the fact I cheat my ass off whenever possible. Mine has a 22 tooth rear sprocket. I might go back to my Sprite 5 for the Tour, next year.
Ted