Typical cost Asphalt shingle roof replacement: $9,000–$18,000 per roofTypical cost Roof repair: $300–$1,500 per repairTypical cost Roof inspection: Free after stormsTypical cost Gutter installation: $600–$2,400 per homeTypical cost Flashing repair: $300–$1,000 per jobMadison Fall tip Get an inspection before winter freeze-thaw cycles begin.Madison Fall tip Clear gutters and downspouts before leaves pile up.Madison Winter tip Avoid walking on icy or brittle shingles.Madison Winter tip Watch ceilings for new stains after snow or ice.Madison Spring tip Check shingles and flashing after heavy snow.Madison Spring tip Photograph any storm damage for your insurance claim.Madison Summer tip Book replacements early; summer schedules fill fast.Madison Summer tip Check attic ventilation before peak heat.