Adding natural light to your home is one of the best upgrades you can make — but up here in the mountains of Stroudsburg, PA, not every skylight contractor understands what that actually takes. The weather in Monroe County doesn’t let up, and a skylight that isn’t installed or maintained with that reality in mind becomes a liability fast. Simon Says Roofing is the skylight contractor that homeowners across the Pocono region trust because we build and service skylights the way this climate demands — tough, sealed tight, and made to last.
A skylight is more than a window in your roof. It changes how a room feels, how a space functions, and how much natural light fills your home through every season. But it’s also a direct opening into the elements, and one that sits right in the path of snow, ice, wind, and rain. Simon Says Roofing handles skylight installation, repair, and replacement for homes and businesses throughout Stroudsburg and the surrounding communities — and we do it with the kind of attention to detail that keeps your roof watertight and your new skylight working the way it should for years to come.
Skylights are one of the most vulnerable points on any roof — and at the elevation and latitude of Stroudsburg, they take a beating that most parts of the country simply don’t experience. Between the weight of snow and ice that piles up through a Pocono winter and the rapid temperature swings that come with spring thaws, even a well-made skylight can run into serious trouble if it isn’t properly installed and kept up.
Here are the skylight issues Simon Says Roofing encounters most frequently on homes throughout the Monroe County area:
The constant freeze-thaw cycle that defines winter and early spring in this region works against skylight seals every single year. Once the seal between the glass unit and the flashing starts to break down, moisture doesn’t just leak in — it creeps in, often invisibly, until the damage is already significant.
The flashing around a skylight is its first and most important line of defense against rain and snowmelt. Up here in the mountains, wind-driven precipitation hits rooflines at sharp angles, and any weak point in the flashing becomes a direct path for water into the ceiling below.
Heavy snowfall in the Poconos means skylights carry real weight for months at a time. Combined with ice that forms as snow partially melts and refreezes, this kind of sustained load stresses both the glass and the frame, and can crack or shatter units that weren’t rated for it.
When the temperature swings between the bitter cold outside and the heated air inside your home, double-pane skylight units are prone to trapping moisture between the glass layers. Once that fog sets in, it doesn’t go away on its own — the unit has failed and needs to be dealt with.
The storms that move through the Pocono Mountains between late spring and early fall can bring hail that cracks or chips skylight glass outright. Even impacts that don’t shatter the unit right away weaken it, and the next round of freeze-thaw cycles finishes the job.
Choosing a skylight isn't as simple as picking a size and cutting a hole in the roof. The pitch of your roof, the direction it faces, how much sun hits that section of the house, and what the framing underneath looks like — all of it matters, especially in a climate like ours. Simon Says Roofing evaluates every one of these factors before we ever start a project. We match the right unit to the right spot, install it with the kind of flashing and waterproofing that holds up through a Pocono winter, and make sure the finished product looks and performs exactly the way it should.
A skylight that's starting to fail doesn't always announce itself right away. Sometimes the first sign is a water stain on the ceiling weeks after the actual breach happened. By that point, the insulation, the decking, and possibly the framing are already wet — and the repair bill goes up with every day the problem sits there unaddressed. Simon Says Roofing offers free, no-obligation estimates on all skylight work, from a brand-new installation to an emergency repair after a storm. One call is all it takes to find out exactly where things stand.
Whether you’re looking to bring natural light into a dark corner of your home for the first time or you’re dealing with an existing skylight that’s seen better days, Simon Says Roofing covers every piece of the process. We work with homeowners and commercial property owners across Stroudsburg, East Stroudsburg, Mount Pocono, Tannersville, and the rest of Monroe County.
Adding a skylight transforms dark spaces by bringing in natural light and improving how the room feels and functions. We manage the entire installation process, including placement, framing, flashing, and sealing to ensure long-term protection against Pocono weather.
Not every skylight problem requires a full replacement when targeted repairs can restore performance. We fix damaged seals, frames, and flashing to make your skylight watertight again without unnecessary cost.
When a skylight is beyond repair due to cracked glass, warped frames, or failed seals, replacement is the best solution. We remove the old unit carefully and install a new skylight built to withstand Pennsylvania’s weather conditions.
Storm damage can quickly lead to leaks through a compromised skylight that needs immediate attention. Our team responds quickly to secure the opening and prevent further damage until permanent repairs can be completed.
A professional inspection helps identify issues before they turn into costly leaks or structural damage. We thoroughly evaluate the glass, frame, flashing, and seals and provide clear recommendations based on the skylight’s condition.
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
It is recommended to inspect your roof at least twice a year, in the spring and fall. Signs include
Contact Simon Says Roofing for expert service, transparent pricing, and quality craftsmanship you can trust.
We provide top-quality des roofing services tailored content
925 N 9th Street
Stroudsburg, PA 18360