Looking for a dependable gutter contractor in Stroudsburg, PA? Simon Says Roofing specializes in professional gutter installation, repair, and maintenance for both residential and commercial properties across Monroe County. We understand how local weather—heavy rain, snow, ice, and seasonal storms—can damage gutters over time.
Whether your gutters are old, clogged, damaged by storms, or simply in need of an upgrade, we offer robust gutter systems, skilled craftsmanship, and clean, organized work sites. Homeowners searching for trusted gutter services in Stroudsburg rely on Simon Says Roofing for quality, reliability, and long-lasting results.




Stroudsburg’s weather can take a heavy toll on gutter systems, causing leaks, overflow, foundation issues, and damage to siding if not addressed promptly.
Some of the frequent gutter issues we encounter include:
Leaves, debris, and dirt often block gutters and downspouts
Intense rain can overwhelm poorly maintained gutters, leading to overflow and water damage
Gutter sections may pull away from the house over time
Ice dams Winter ice buildup can block gutters, causing water to back up behind fascia boards
Incorrectly pitched gutters prevent proper drainage
From installations and repairs to inspections and custom gutter solutions, our certified team is committed to safeguarding your property. We make the entire process easy, clear, and worry-free—from your first inquiry to the completion of the project.
Don’t let minor gutter issues turn into major headaches. Whether you need repairs, a full replacement, or a professional inspection, schedule a free estimate with Simon Says Roofing today. Exceptional service, dependable work, and peace of mind are just a call away.
Simon Says Roofing provides comprehensive gutter solutions for homes and businesses throughout Stroudsburg and nearby communities.
We offer full gutter replacement using premium materials that are built to withstand the elements. Our expert team ensures a smooth, precise installation that protects your property and improves its curb appeal.
Our repair services address leaks, separated joints, sagging sections, and other gutter problems before they escalate. We provide effective, long-lasting solutions to restore your system’s performance.
When sudden gutter damage occurs, our emergency team responds quickly to protect your home or business. We provide fast temporary or permanent solutions to prevent further water damage.
Regular inspections help identify potential issues before they become costly repairs. Our detailed evaluations include clear reports and honest recommendations tailored to the condition of your gutters.
After severe weather, we conduct thorough assessments to determine the impact on your gutters. We document all damage and guide you through the repair process, including assistance with insurance claims if necessary.
The answer usually comes down to where the problem is and how far along it’s gotten. If the issue is limited to the flashing or the seal around the frame and the glass itself is still solid, a repair is very likely the smarter and more cost-effective route. But if the glass is cracked, the frame has warped or rotted, or moisture has been getting between the panes for a long time, you’re looking at a replacement. Simon Says Roofing will come out, assess the unit in person, and give you an honest breakdown of what makes sense for your specific situation, we’re not in the business of selling you a new skylight when a repair will do the job just as well.
The price of a skylight installation in the Poconos depends on several things: the type of unit you’re going with — fixed, operable, or tubular — the size, the material of the frame, and what the framing situation looks like underneath the roof where it’s going in. Steeper roof pitches and older homes with non-standard framing can add to the labor side of things. For most single skylights on a straightforward residential roof in Monroe County, the total cost lands in a moderate range, but that number moves based on your specific property. Simon Says Roofing gives you an itemized estimate for free before anything starts, so there are no surprises when the work begins.
That fog you’re seeing between the two panes of glass is moisture that’s gotten trapped inside the sealed unit — and once it’s in there, it doesn’t come out on its own. It usually happens because the seal between the panes has degraded over time, often sped along by the kind of temperature swings the Poconos see between winter and summer. Unfortunately, a fogged-out double-pane skylight can’t really be repaired by cleaning or re-sealing from the outside — the unit itself has failed and needs to be replaced. The good news is that modern replacement units use improved sealing technology that holds up significantly better, and Simon Says Roofing installs them with the kind of flashing and waterproofing that keeps moisture out from the start.
Skylights can work on most roof types, but not every roof is equally well suited for them — and the installation method changes depending on what you’re working with. A standard gable or hip roof with a moderate-to-steep pitch is the most straightforward setup, which is good news for a lot of homes in the Stroudsburg area. Flat or very low-pitched roofs require a different approach, typically a curb-mounted unit or a tubular skylight that can thread through attic space. Shingle roofs, metal roofs, and even slate or tile can all accommodate skylights when the right unit and the right installation technique are matched together. Simon Says Roofing will take a look at your specific roof and tell you exactly what will work before you commit to anything.age
Simon Says Roofing has been handling skylight work for homes and businesses across Stroudsburg and the wider Pocono region for years — and we know exactly what it takes to put a skylight in up here and have it actually hold up. If you’re thinking about adding one, if you’ve got one that’s giving you trouble, or if you just want to know what you’re working with before the next winter comes around, we’ll come out and give you a straight answer at no charge. Call us at (570) 202-6631 or get in touch online to set up your free estimate today.
We provide top-quality des roofing services tailored content
925 N 9th Street
Stroudsburg, PA 18360