You can measure a roof from the ground, as long as you correct for the slope. Here is the method, the multiplier table, and a worked example you can follow with your own numbers.

Step 1: measure the footprint

Measure the building as if you were looking straight down at it — length by width, in feet. Do not try to measure along the slope. For a simple gable roof on a 40 by 30 foot house, the footprint is 1,200 square feet.

If the roof has several sections, break it into rectangles, measure each, and add them together.

Step 2: find the pitch

Pitch is written as rise over run: how many inches the roof climbs for every 12 inches it travels horizontally. To measure it, hold a level against the roof surface, mark 12 inches along it, and measure straight down from that mark to the roof. A 6 inch drop is a 6/12 pitch.

From inside the attic works just as well, against a rafter, and you do not have to get on the roof at all.

Step 3: apply the multiplier

The sloped surface is always larger than the footprint. The multiplier is the hypotenuse of the pitch triangle:

Our 1,200 square foot footprint at 6/12 becomes 1,200 × 1.118 = 1,342 square feet of actual roof. Ignore this step on a steep roof and you will be short by a third.

Step 4: add waste, then convert to squares

Add 10% on a simple gable roof and 15% once there are valleys, hips or dormers, because those force angled cuts that cannot be reused. 1,342 + 10% = 1,476 square feet.

Roofing is sold by the square, which is 100 square feet. That is 14.76 squares, so you order 15 squares — suppliers deal in whole squares. At the usual 3 bundles per square, that is 45 bundles.

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What the square count does not include

Squares cover the field of the roof only. Ordered separately, and all by the linear foot rather than the square:

Measure the ridges, hips, eaves and rakes with a tape on the plan or from the ground, and price those separately.

A note on layers

Most codes allow two layers of asphalt shingles on a roof. If there are already two up there, you are paying for a tear-off as well, and that changes the job far more than the shingle count does. Count the layers at a rake edge before you price anything.