I've been in the roofing and siding business for 30 years, and during that time have installed hundreds of cedar shingle roofs. They're a great option in coastal New England, where I live and work, and are a natural fit for the area's many capes and shingle-style homes. Also, a lot of the homes we work on are just steps from the Atlantic Ocean and have to endure frequent high winds. Knowing that wood shingles are more wind-resistant than asphalt helps us sleep better during winter storms.
On the downside, a wood roof costs more than an asphalt one - about twice as much, on average. And a good cedar roof's service life of around 30 years trails the 35 years you can expect from today's best architectural-grade asphalt shingles. Still, for many of our clients, the pros of wood outweigh the disadvantages.
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