A simple rectangle roof is the easiest of all to calculate. This is the kind of roof found on a shed, with just one flat rectangular surface. You simply multiply the length by the width of the roof line, and this will give you the square footage. For a gable roof, measure the surface from the wall line to the peak. Multiply width times length, and multiply the result by two.
Triangles in a roof get tricky to calculate. The formula for area of a triangle is one half of the base times the height. You have to look at your roof sections, and lay out the triangles formed by where the dormers meet the main roof. Iko Roofing recommends you draw your roof on a flat piece of paper with all the measurements you took, and calculate the roofing area. A qualified architect or experienced roofer can assist you with this.
Overhangs are another tricky area to calculate. Your original measurements may have been from the wall, but an overhang adds significant area to the roof line. The University of Central Florida specifies how overhangs on passive solar homes are designed. You have to calculate the square footage of the overhang. Again, a qualified roofer can assist you with this.
No human being is perfect, and in the process of installing a roof, mistakes will be made. When a mistake is made, the shingle will have to be torn out, and a new shingle installed. Allow 5 percent extra for the goof factor so you don't run short on roofing. Ask the building supply company if they allow returns. It is better to buy too much and return the unused shingles than to run out.
All roofing shingles are sold by the "square." A square is 100 square ft, or an area that is 10 ft by 10 ft. Shingles are sold in bundles. A bundle is 33 1/3 square feet. To calculate how many bundles you need, first calculate out the total square feet of roofing needed. Divide this figure by 33 1/3. This will give you the number of bundles needed. Round up the leftover fraction to compensate for the goof factor.