Rent
Neck and neck
Winston Salem and Richmond are about even on rent.
Winston Salem
$2,150/mo
Richmond
$2,150/mo
What this means for your life
Typical rent in Winston Salem is $2,150 a month versus $2,150 in Richmond, close enough that housing cost should not decide the move by itself. Factor it into your budget alongside salary differences between the two markets, then pick the city that wins the categories you actually live in: safety, schools, pay, or weather.