A.:
Smart move asking about Bolingbrook/Romeoville. That is my home town. I wouldn't recommend Winston Woods. While that little subdivision is ok, it is surrounded by some really nasty elements.
The west side of bolingbrook is good. If you can find something in Peppertree (tell your RealEstate Agent) you will be doing well. Finding something in Bolingbrook under 200 is almost impossible.
In Romeoville - try again for the west side. STAY AWAY from any thing East of Weber and South of 135. Anything Hampton Park should be good and extremely affordable. These are 40 year old homes which some have been kept up well.
Being a product of that school system, you might want to start your kids out at St. Andrews Catholic School. That is what i did. The grade schools and especially the jr high is not the greatest.
Send email if you have more questions, I would be happy to answer them.
C.