I grew up in Winsford, but left just over 20 years ago when I went to Uni. Parents moved nearly 10 years ago to be closer to me when I had kids.
It will have changed a lot in the 20 years since I lived there, there has been an awful lot of house building since then which has lead to the sprawl of the place - for a while I worked in the Community Charge dept of the district council and was more than once given a Winsford address as Chester by people buying on the new estates on that side of town who didn't want to have a Winsford address.
Historically it was a small village (well more than one - Over, Wharton, Darnhall etc) and then in the 60's when they cleared out the slums in first Manchester and then Liverpool they built a number of large council estates to house people moved out from those cities.
Unfortunately that was followed by an economic downturn and loss of jobs on the industrial estates that were also built - which resulted in at least one generation growing up with non-working parents and other relatives, and little expectation of finding work themselves.
My mum taught on one of the estates and my dad was a policeman, so I probably had more exposure to some of the less attractive aspects of the town.
Having said that when growing up (70/80's) I lived in nice enough areas with easy access to open space (Knights Grange - which I think is mostly built on now) within easy walking access, and within the heart of Cheshire and access to all that enabled.
I don't think that with Cheshire to choose from that Winsford is somewhere that I would be drawn to, but then I am currently considering a move to a town that is similar in many ways - because as my children (primary school) get older I think that a town has benefits over a village location.