How many shingles do I need?
Roof area divided by bundle coverage, plus waste. One bundle of shingles covers 33.33 sq ft and 3 bundles make one square (100 sq ft). With 10% waste, 1,732.05 sq ft of roof needs 58 bundles — about 19.3 squares, so order 20 squares if you buy by the square.
Use the roof area, not the footprint: a 1,500 sq ft footprint at a 30 degree pitch is 1,732.05 sq ft of roof, so the footprint alone would leave you short. Add 10% waste for a simple gable roof and 15% for a cut-up roof with valleys, hips and dormers.
Working out the roof area from your footprint and pitch? Use the roofing calculator.