Tod and Hebden are similar although Tod is a bit more low rent (sorry, Tod dwellers). They are both an absolute pig to get to tho (long way off the motorway on congested roads. Some nice properties in and around Sowerby Bridge which is closer to the M62 and Halifax.
Apologies for the misleading Sheffiled rail comments - I did a quick check and it seems things have improved since I last looked, when it took about 4 hours to get to London.
I honestly would avoid Richmond - if you want something like that then Ripon is similar and better connected.
I also second Helmsley as it's lovely.
Further up maybe take a look at Saltburn in Middlesborough
And finally can I suggest Otley? Easy access to Leeds and the Dales, nice town feel, loads of great pubs, live music and lively theatre scene including comedy, lots of pretty stone houses, campaign to reopen the Lido, annual show/ carnival, farmers market, excellent high school. Close to Leeds Bradford Airport too.