Property owners can have a hard time telling when they should get a new roof, especially if they never see their roof. There are a couple of signs that will be a sure giveaway: (1) shingles in the yard, (2) leaky roof, (3) shingles are broken, torn, cupped, curled, or appear to be a claw, (4) your neighbors are getting their home reroofed, and/or (5) the roof is sagging. Another good sign is the amount of time since the last reroofing. Most roofs last about 25 years, so if it's been that long or more, you should start accepting free quotes.