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27 squares is equivalent to 2700 square feet. Measure square area by multiplying length by width of your entire roof. Add all the areas together for total square feet. Take the square feet and divide by 100 to get squares. 3 bundles of shingles to make one square with 5 inches of exposure on the shingles. For every 33 feet of ridge you will need one bundle of three tab shingles. Each bundle of shingles has 27 shingles so that is 81 single tabs at approximately 5 inches each, 405 inches of run or 33.75 linear feet. At current shingle prices near $21 per bundle that will cost you about $1700 just in shingles. #15 roll of felt is 4 squares at about $20 per roll. One box of coil nails will usually cover 18-20 squares. Any other calculations and you are on your own.

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Q: What is 27 squares in roofing measurement?
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