Standing seam and metal panel roofing, roof repair and full replacement in Chestertown. We show up when we say we will, and we clean up before we go.
Metal roofing is our specialty, but shingles, gutters, soffit and leak work all get the same attention in Chestertown.
Hard wind lifts shingles and works panel fasteners loose along the edges, which is exactly where the next storm gets underneath. We refasten, replace and reseal.
We work around your hours, weekends included when that is what it takes to keep your doors open while the roof goes on.
Full tear off, decking checked board by board, then a new metal or shingle roof over proper underlayment. You get the price and the start date before anything comes off.
Ice backs up at a cold eave and pushes water sideways under the roof. We clear it without gouging the panels or the shingles.
If two other people have caulked it and it still leaks, call us. Most stubborn leaks turn out to be flashing, a valley, or a fastener nobody thought to check.
Low slope roofs fail at the joints and around anything that sticks through them. That is where we start, not out in the middle of the field.
Careful footwork, matched materials, and flashing done the way it was done when the roof went on.
A limb through the roof or panels peeled back overnight needs covering now, not next week. We get it dried in first so the inside of the house stops taking damage.
Old skylights leak at the flashing long before the glass ever fails. We reflash, reseal, or set a new unit and tie it in properly.
We repair what the storm actually broke. If that is one slope, we do one slope, and we will not pad an estimate to make a claim look bigger.
A twenty year old panel roof usually needs fasteners and sealant, not replacement. We refasten with new washers and get you another long stretch out of it.
Rotted fascia and sagging soffit let water and animals in behind the roof edge. We cut the bad wood out and put new in.
A coating buys real years on the right roof and wastes money on the wrong one. We will tell you honestly which kind you are looking at.
Lifted panels, missing shingles, flashing that has given up where the chimney comes through. We find what is actually wrong, fix that, and leave the rest of your roof alone.
Guards and screens so you are not up a ladder every fall digging pine needles out of the gutter by hand.
A metal roof is the one that outlives the mortgage. We install exposed fastener panels and standing seam over solid decking and real underlayment, with around twenty standard colors to choose from.
A shingle repair should not be visible from the street. We match as close as the weathering allows and blend the new work into the old.
Buying, selling, or just want to know how many years you have left? We look, we tell you, and we do not turn it into a pitch for a roof you do not need.
Hail bruises shingles and dents the softer metal on vents, valleys and gutters. We show you what we find and document it properly for the claim.
Waterproofing details on additions, porches and low slope tie ins, where two roofs meet and most leaks quietly begin.
A metal roof is the thing we do best. Our family has been installing them out of Morganton, North Carolina since 2002, and our crews bring that same work to Chestertown: standing seam, exposed fastener panels, and ridge and valley trim that fits instead of being forced.
Shingles still make sense on a lot of Chestertown houses, and we will say so when they do. What we will not do is talk you into metal when your budget or your roof does not call for it. Estimates are free either way.
Here is what Chestertown homeowners tell us makes the difference.
The same family started this company putting metal roofs on neighbors houses in 2002. It has never been sold, franchised or handed off to a call center.
If your roof needs a repair and not a replacement, we say so. Plenty of our best customers are people we talked out of a job they did not need yet.
Around twenty standard metal colors, and the chart comes out with the estimate so you can hold it up against your siding and shutters before you commit.
You get a start date and we hold to it. If weather moves your job we call you, rather than leaving you watching the driveway.
Standing seam and metal panel roofs are the work we are known for. Color, trim, fastening pattern — we have done hundreds and we will walk you through all of it.
The questions that come up on just about every estimate we write.
For most Chestertown homes, yes. A metal roof costs more up front than shingles, but it usually outlives two or three shingle roofs, sheds rain and snow better, and does not peel off in a hard wind. We will price metal and shingle side by side so you can compare real numbers instead of guessing.
Plenty of them. Most Chestertown customers choose from around twenty standard colors, and green, burgundy, bronze, black, gray, tan and barn red are the ones people pick most. We bring the color chart out with the estimate so you can hold it up against your siding.
Often, yes. Plenty of the Chestertown roofs we get called to look at need flashing reworked or a section refastened, not a whole new roof. We will tell you honestly which one you are looking at, and if it is repairable we would rather repair it.
No. Estimates are always free in Chestertown. We come out, measure, look in the attic if we can get to it, and leave you a written price. Nobody will push you to sign anything that day, and the number does not expire in an hour.
A typical Chestertown shingle roof runs roughly $8,000 to $18,000 in 2026 for an average single family home, and more if the deck has rot or the roof is steep and cut up with dormers. We do not price off a satellite photo — somebody comes out and measures.
Any dry stretch works. We roof in Chestertown year round, though we schedule shingle work for when it is warm enough for the strips to seal properly, and we watch the forecast so your house is never left open overnight.
Real feedback from homeowners whose roofs we have worked on.
"Metal roof on the barn and one on the shed while they were already out here. Good work on both and the price was fair for that much steel."
"Thank you so much to the entire crew at Roofing Brothers for our amazing new tin roof! You were amazing to work with and I couldn't recommend you to others enough! Great communication, pricing, color options, efficiency, and HONESTY! If anyone needs a new roof, I highly recommend this crew! Phenomenal job."
"They reroofed the porch and matched it to the house so well you cannot tell where the old work stops and the new starts."
Our crews cover the surrounding area, not only the city limits.