Pocono winters are hard on roofs. Freeze-thaw cycles, ice dams, heavy wind, and hail all take their toll — and the damage doesn’t always show up right away. Simon Says Roofing handles roof repairs across Monroe County fast, clean, and done to last.
Don’t let a small problem turn into a big one. One cracked shingle or a loose piece of flashing can let water into your roof system and start damage you won’t see until it’s expensive. Call Simon Says Roofing and we’ll find it, fix it, and seal it up tight.
Roofs in the Poconos take a beating that most areas of the state don’t see. Here’s what Simon Says Roofing runs into on a regular basis:




We get on your roof and track the problem down to exactly where it is. No guessing, no assumptions.
We repair what needs repairing — shingles, flashing, sealant, whatever the job calls for — and seal everything back up properly.
Your yard looks the same when we leave as it did before we showed up. No nails, no debris, no mess.
We handle every type of roof repair that homes and businesses across Stroudsburg and the Pocono region need. Here’s what that looks like in practice.
Missing, cracked, or curling shingles get replaced with a match to what's already on your roof. We don't leave a patchwork — we make it look right and hold up the way it should.
Loose, rusted, or separated flashing around chimneys, vents, and valleys gets reset, re-sealed, or replaced. This is where most roof leaks in the Poconos actually come from.
If water is getting in, we find where it's coming from — even if the entry point isn't where the drip is showing up. We stop the leak and seal the source, not just the symptom.
Ice dams tear into shingles and flashing every winter up here. We repair the damage they leave behind and reinforce the edges so the next freeze doesn't do the same thing all over again.
Storm just hit? Roof is open and rain isn't stopping? Simon Says Roofing responds to emergency repairs across Monroe County as fast as we can — securing the roof and stopping the water before more damage builds up.
We're based in Stroudsburg and we work in Pocono weather every single day. We know exactly what does damage up here and exactly how to fix it — not guess at it. We use the right materials, we seal everything the way this climate demands, and we don't leave until the job is done right. One call, free estimate, no pressure.
It depends on the size and type of the repair — a few shingles will run a lot less than a flashing replacement or an ice dam repair. Simon Says Roofing gives you an exact number upfront, no surprises. Call us for a free estimate and we’ll tell you exactly what it’s going to take.
A good repair on a roof that’s still in solid shape overall can hold up for years. But if the roof is aging and the damage keeps coming back in the same spots, at some point a replacement makes more sense. We’ll be honest with you about which one your roof actually needs.
If it’s an emergency, we move fast. We respond to urgent roof repairs across Monroe County as quickly as conditions allow — especially when rain is still coming down and the damage is getting worse by the hour. Call us and tell us what’s happening.
If most of the roof is still in good shape and the problem is isolated, a repair is the smarter move. If you’re patching the same spots year after year or the shingles are worn across large sections, it’s time to talk about replacement. Simon Says Roofing will give you a straight answer — no upselling.
Simon Says Roofing fixes roofs across the Pocono Mountains — fast, clean, and built to last. Call (570) 202-6631or reach out online for a free estimate today.
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925 N 9th Street
Stroudsburg, PA 18360