That sprocket is definitely gonna be your best clue as to the maker of the bike; i know i've seen it before, but i can't place the marque with the sprocket. At an rate, the frame is almost certainly NOT Nottingham- (Raleigh-) built, as the drop outs are wrong. FWIW, I'd trust that this is a pre-1960 bike. Also, FWIW, Tube Industries bought Raleigh out in 1960; TI already owned the BCC conglomerate, and when they purchased Raleigh, they also purchased the rights to all of the marques that Raleigh had bought previously (Rudge, Humber, Triumph, the BSA group) as well as all of the lower-end Raliegh brands, like Robin Hood and Armstrong. Raleigh's Nottingham factory was the biggest and most productive, so that's the one that TI kept going (prior to that, the TI' biggest producer was Phillips).... so, we know that this bike is not made in Nottningham, which makes it most likely a pre-1960 bike....
And yeah, I wouldn't go 2grand for this bike, but i'm not surprised that someone else is gonna. It's not a real Hendee/Mass Indian, but i'd expect it to sell for far more if it was. Cool bike regardless.