Mark Solomon- Owner No matter what part of the U.S. you live in, winter has its own challenges for homeowners. Here are some fall maintenance jobs smart homeowners do to make sure their homes are all set for winter. Check and clean gutters- Gutters can collect leaves and debris over the summer and fall. Clean them to make sure wintertime rain or snow don't cause problems. Inspect the roof- Check for missing, curled, or cracked shingles. Look for damaged metal flashing