A house I'm looking at needs its roof replaced in a few years.  How much does that typically cost around here?  The house is a little shy of 1,000 sq. ft. and I'd be putting your standard asphalt shingles on.

I use a website called HomeAdvisor that can give you ballpark figures down to the zipcode (labor rates can vary a lot nationwide).  You can look up anything from painting costs to replacing the roof.

I just put a roof on a 1100 sqft ranch and it cost me $4500.

I'm semi local to you and I got a 1,100 sq. ft house and single stale garage done for 3K. This was through a connection and very cheap. The second cheapest quote was for $4,200 which also is a good deal.

Hey Shawn! I think you can get a decent estimate for a simple roof re-shingling in the $4-6 per sqft range. Plan for the high side and know you might have some margin to gain back. That's better than underestimating. This will vary also dependent on the complexity of the roofline and the pitch. It will also vary if there is more than one layer to tear off.

You also need to consider the possible re-sheeting or repairs to the decking. We have often gone over a single layer of old shingles but wouldn't always do it on a long term hold.

Pitch of the roof, access, decking quality? Generally (very, very general), I was able to find capable people (with insurance, who gave me a tax ID so I could deduct, etc., etc.) who were around $300/square.

Cost me $5,570 for a 800+ sq foot house. Job well done but a little pricey compared to what was quoted above.