1 Common materials for a wooden roof are red cedar shake shingles and yellow pine. 2  Expect to pay between $100 and $200 per square for wood shakes and shingles. 3  The price including installation is $200 to $325 per square foot.4  For an average-sized roof of 2,000 square feet, this works out to $4,000 to $6,500. Expect to pay between $100 and $200 per square for wood shakes and shingles. 2  The price including installation is $200 to $325 per square foot. 3  For an average-sized roof of 2,000 square feet, this works out to $4,000 to $6,500.