New Roof Needed?

Found a piece of roofing shingle in a flower bed at the weekend. Not an expert (yet) but it is probably the asphalt type. Got out the binoculars--there are several places where a 3 to 4ft wide piece of shingle is missing, essentially all of the shingle that sticks out from under the shingle above it, but the edge of the remaining bit is ragged.
It looks like there are shingles of a different color underneath. There was maybe 1/2" of granular material in some of the gutters when I cleaned out the leaves last autumn.
House is about 30+ years old. Don't know how old the roof is since we've only been here a year, but it's probably over 10 years old.
I'm guessing I may be looking at a new roof. Is it common practice to put shingles over older shingles? How many layers can you go? Or does it make more sense to remove existing shingles back to the wood?
Any thoughts welcomed. I won't be doing the work myself.
Greater Richmond, Virgina area.
Thanks, Sam
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Two layers is usually the max. Check with yout local codes. It makes more sense to remove the two layers down to the substrate. Tom
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I mean "your" local codes. Tom
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You get the best job by removing existing shingles back to the wood.

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30 year old home, almost certainly original roof. Deposits in the gutter is a sure sign of needing a new roof. About a month away from doing my own. Would be best advised to strip off all old to be able to inspect the wood underneath.
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Sounds like more than one layer I would strip it because of the weight. If you have any ceiling damage from leaks you may have wood damage too. Go with a roofing company not a siding or painting etc... get a Master Elite contractor or the likes, get a warranty from the manufacturer and installer as well. The Golden Pledge warranty is a good one

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