Roofing in Connecticut starts with an older roof that has already been patched in more than one decade. Slate still covers houses in New Haven, Hartford's orbit, and the older shore towns, and it fails at the nails and the valleys. Asphalt on capes and ranches fails at the eaves, where ice backs water under the tabs. Sound wind lifts edges that inland snow only weighs down. Name the material and the slope.
Chimney flashing on a colonial is the usual path into a plaster ceiling. A cricket was never built, so leaves and ice sit on the uphill side and melt sideways. Skylights cut into a later dormer drip at the curb. Porch roofs tied into the main house open at that seam. If you can see the attic, say whether the sheathing is wet or the drip only shows up in a thaw on the ceiling below.
A second layer of shingles over a soft deck is common and it hides the real job. Underlayment and a metal edge at the eave decide whether next winter repeats the stain. Ventilation in a Cape attic that was finished without a path for air will cook the roof and ice the overhang at the same time. Tell the caller if the attic is storage, living space, or both.
Salt air along the Sound is hard on flashing metal and on fasteners. Inland oak leaves fill valleys and hold damp against the tabs. Moss on a north slope in Litchfield County is a clue, not a charm. Note solar mounts, snow guards, and any antenna still lagged through the ridge. Those holes are part of the roof even if you do not use them anymore.
Say the town, slate or asphalt or something else, and whether water is coming in now. A missing tab after a wind off the water is a different call from a yearly ice dam over the kitchen. Mention a sagging ridge if you can see it from the yard. Do not walk a slate roof to get a closer look. Call the number on this page.