A roof in the Pocono Mountains doesn’t just sit on top of your house and look good from the curb. It takes the full force of everything this region throws at it — punishing winters with heavy snowfall, ice that builds up and tears apart shingles and flashing, freeze-thaw cycles that crack and shift material month after month, and storms that come in fast and hit hard. Finding a roofing contractor in Stroudsburg, PA who actually understands what that means for your home isn’t always easy. Simon Says Roofing does. We’ve been working on roofs across Monroe County long enough to know exactly what this climate does — and exactly how to build against it.
Your roof is the single most important layer of protection your home has. Everything underneath it — the framing, the insulation, the walls, the foundation — stays dry and intact because the roof is doing its job. The moment it starts failing, the cost of what follows adds up fast and quietly, long before you notice anything from inside the house. Simon Says Roofing handles roof installation, repair, replacement, and everything in between for residential and commercial properties throughout Stroudsburg, East Stroudsburg, Mount Pocono, and the wider Pocono region. We use the right materials, we install them the right way, and we
From the first nail on a brand-new build to an emergency patch job in the middle of a storm, our crew covers every piece of roofing work that homes and businesses in the Pocono Mountains need. Here’s exactly what we do.
Simon Says Roofing installs new roofs using architectural shingles, metal roofing, and other systems built for the Pocono climate. We layer in proper underlayment, ice and water shield along every vulnerable edge, and ventilation that keeps your attic breathing the way it needs to year-round.
A missing shingle, a cracked flashing, a soft spot after a hard rain — these things don't stay small for long. Simon Says Roofing finds exactly where the problem is, fixes it, and seals everything back up without tearing apart sections of the roof that are still holding up fine.
A storm doesn't wait for business hours, and neither does the damage. Simon Says Roofing responds to emergency roofing situations across Monroe County fast — securing the roof, stopping the water, and protecting your home before the next round of weather hits.
A lot of roofing problems start invisible and don't show up as a leak until the damage is already done. Simon Says Roofing gets up there and checks everything — shingles, flashing, ventilation, ridge caps — and gives you an honest report on what's holding and what isn't
After a serious storm, documenting the damage the right way matters as much as fixing it. Simon Says Roofing conducts thorough post-storm assessments, photographs everything, and helps you put together exactly what your insurance company needs to process the claim.
When a roof is worn past the point where repairs make sense, Simon Says Roofing tears it off completely, inspects the decking and framing for any rot underneath, and puts down a new system from scratch — built to handle what the Pocono climate actually does.
Simon Says Roofing is based right here in Stroudsburg. We work in Pocono weather every day — we know what a roof looks like after a brutal winter, what a summer storm does to shingles and flashing, and exactly what it takes to build something that holds up through both. The materials we install are chosen for this climate specifically — architectural shingles from manufacturers like GAF and Owens Corning, metal roofing systems rated for decades in harsh conditions, and proper ice and water shield along every edge where freeze-thaw damage hits hardest. Every roof we put down gets the ventilation it needs to keep moisture out of the attic the way it does when that part of the job gets skipped. The way we work is straightforward: you call, we come look at your roof at no charge, we tell you what needs to happen and what it costs, and we do the job clean and on schedule. If something comes up down the road that's covered under our work, you call and we handle it. No runaround.
Don’t wait for small roofing issues to turn into costly problems. Whether you need a repair, a full replacement, or a professional inspection, Simon Schedule your free estimate with Simon Says Roofing today. Quality work, honest service, and peace of mind start here.
The short answer is that it depends on how much of the roof is still in good condition and where the problems are concentrated. If you’ve got a handful of damaged or missing shingles in one area — say, after a storm or around a chimney or vent — and the rest of the roof is holding up, a repair is usually the right call. But if the shingles are curling across large sections, the granules have worn off to the point where you can see the mat underneath, or you’re seeing damage in multiple spots spread across the whole roof, you’re probably looking at a replacement. Simon Says Roofing will come out, take a hard look at the whole thing, and give you a straight answer — we’d rather tell you a repair will do the job than sell you a new roof you don’t need yet.
For most homes in the Stroudsburg area, architectural asphalt shingles — sometimes called dimensional shingles — are the most practical choice. They come in a wide range of styles and colors, they’re designed to handle wind and impact better than basic three-tab shingles, and quality brands like GAF and Owens Corning offer products with warranties that back up the performance claims. Metal roofing — steel or aluminum — is the other strong option, especially if you’re looking for something that will last forty or fifty years without much maintenance. Metal holds up exceptionally well against the freeze-thaw cycles and heavy snow loads that the Poconos produce every winter. The tradeoff is a higher upfront cost, but over the life of the roof, it often ends up costing less than replacing asphalt shingles two or three times. Simon Says Roofing can walk you through both options based on your home, your budget, and how long you plan to stay.
For a typical single-story home in Monroe County, a full roof replacement usually gets done in one day — sometimes two if the roof is particularly large or the weather cooperates only partially. Two-story homes, properties with complex rooflines — multiple valleys, dormers, chimneys, or steep pitches — and bigger square footages will take longer, sometimes stretching to three days or a little more. Simon Says Roofing gives you a realistic estimate of the timeline before the job kicks off. We know that having a crew on your roof and a dumpster in your driveway is disruptive, and we move as fast as the job allows without cutting corners on the installation. Most homeowners in Stroudsburg are surprised at how quickly it goes from start to finish.
First, get the water away from anything it’s going to damage. If it’s dripping into a room, put buckets or towels down and move anything valuable out from under it. If you can safely get into the attic, take a look for where the water is actually coming in — it’s not always directly above where it’s dripping, because water follows the framing and decking until it finds a low point. Do not get on the roof yourself in wet or icy conditions — that’s how people get seriously hurt. Call Simon Says Roofing. If it’s an active emergency, we respond as fast as we can to get up there, find the source, and stop the water from getting in. A temporary repair will hold things until we can do the full fix properly — but the sooner we get eyes on it, the less damage builds up in the meantime.
In most cases, yes — standard homeowner’s insurance policies cover damage caused by wind, hail, ice, and other weather events that fall under the category of sudden and accidental loss. What insurance typically doesn’t cover is wear and tear — shingles that have just aged out, a roof that was already in rough shape before the storm hit, or damage that’s been sitting there unaddressed for a long time. The key is getting the damage documented properly and quickly after the event. Simon Says Roofing does storm damage assessments and helps put together the documentation your insurance company needs to process the claim. We’ve been through this enough times to know what the process looks like from start to finish — and we make sure you’re not left figuring it out on your own when you’ve already got enough on your plate.
Simon Says Roofing handles everything from brand-new installations to emergency repairs — and everything in between — for homes and businesses across Stroudsburg and the Pocono Mountains. If your roof needs attention, if you’re not sure what shape it’s in, or if a storm just came through and you want someone knowledgeable to take a look, pick up the phone or reach out online. Free estimate, no pressure, no
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925 N 9th Street
Stroudsburg, PA 18360