Why does the flashing around my chimney leak?
Because it is a layered metal joint set against brick and exposed to every rain. Sealant dries and cracks, metal corrodes or lifts, and the mortar it was set into can crumble. Any of these opens a path for water behind the shingles.
A properly built chimney joint sheds water in layers, and each layer overlaps the one below. Step flashing runs up the side of the chimney, woven in with the shingles. Counter flashing is set into the brick and hangs over the step pieces. If any of those layers is missing, only caulked or unfastened, the water finds the gap.
Tar or caulk smeared along the joint is a common sign of past trouble. It can buy time, but it hides the actual failure and tends to crack within a season or two.
Do the older neighborhoods have more chimney problems?
They have more chimneys, and older ones. West End, Ardmore and Buena Vista have many masonry chimneys on houses a century old or close to it, and flashing set decades ago may never have been redone. Those houses get chimney leaks more often than simple newer ones.
The West End Historic District has 508 contributing buildings, built from about 1887 to 1930, and Ardmore is the city's largest and newest historic district at 600 acres. The Reynolda Historic District covers 178 acres on Reynolda Road. Brick chimneys come with the styles of those neighborhoods, and so does a lot of roof complexity around them.
A roof can be re-covered several times while the chimney joint is left alone. That is how a roof with fresh shingles still leaks at the chimney.
Is it the flashing or the chimney itself?
Either, and sometimes both. Flashing leaks show at the roof-to-chimney joint. Masonry leaks come through cracked mortar, a damaged crown or a missing cap and show lower down or inside the flue. A roofer can say which side a problem sits on and refer the masonry part.
Brick is porous and mortar breaks down with freeze-thaw cycles. Winston-Salem has a snowy period running from about November 29 to March 16, and water that gets into a mortar joint and freezes widens it. That is a masonry problem that flashing will not fix.
If the roofer points to cracked mortar or a damaged crown, ask a mason or chimney specialist to look. A chimney repair is a separate trade from roofing, and one contractor may not do both.
Do I need approval to fix chimney flashing on a historic house?
It depends on the district and the work. Roof replacements in West End, Old Salem and the West End Historic Overlay District go through the Forsyth County Historic Resources Commission for a Certificate of Appropriateness. Ask before changing visible materials, including metal.
City records show roof replacements in the West End and Old Salem going through the commission, with staff-level approval for minor work and a commission agenda for larger changes. Whether a flashing repair counts as minor work is a question for the commission's staff, not for this site.
See historic district roofing for how that review works in practice.
What can I check myself before calling?
From the ground you can look for rust streaks, gaps between metal and brick, and smeared tar. Inside, look at the attic framing and the ceiling beside the chimney after rain. Notes on when the stain grows help a roofer decide where to look first.
Note whether the stain gets worse in wind-driven rain, in a long soaking rain or only after snow melts. Those patterns point to different parts of the joint: a gap in counter flashing, a failed cricket seam or water coming through masonry.
Take photographs of the chimney from several angles, and of the stain inside with something in the frame to show where it sits. Do not climb up to look. A roofer who can see the joint up close gives a better answer than any view from a ladder.
