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100 sq ft = 1 square.
The same as it is anywhere else on the house. A square is 100 square feet. It is a measurement that is used with siding or flooring also.
If you mean square feet, there are 100 square feet in a square. So 20 squares is 2000 square feet.
100 sq ft = 1 square.
500 square would be 50,000 square feet. Not knowing in what context this is used, it could be that it should read or mean 500 square feet which would be a small roof. 50,000 is a very large roof. Shingles are figured in squares. 1 square is 100 square feet made from 3 bundles of shingles on average. That is just how a roof is figured so that there is a common reference point.