Roofing Contractor in Winchester, MA
Roof replacement and repair for Winchester homes, including the larger older houses with complicated rooflines.
Owner run, 40 years roofing this part of Middlesex County.
Winchester homes tend to be larger and older than average, and that makes the roof a bigger job than it looks like from the driveway. Multiple planes, dormers, valleys running into valleys, and a porch or addition roof off the back that is flat while the main roof is steep. There is more going on up there than on a straightforward gable, and more places for it to go wrong.
Mark Brady Roofing has worked on roofs in this area for 40 years. Roof replacement, roof repair, flat and low-slope sections, storm damage, gutters, skylights. We are owner run, so Mark and Glen are the ones who go up and look at the roof and the ones who are there while the work happens.
Roofing Services in Winchester, MA
Roof Replacement in Winchester. Full tear-off, decking inspected and replaced where it is bad, then a complete system with proper ice and water shield, underlayment, and ventilation.
Roof Repair in Winchester. Leaks, failed flashing, damaged valleys, worn pipe boots, storm damage. A good number of the roofs we look at need a repair rather than a replacement, and we say so when that is the case.
Flat and Low-Slope Sections. Porch roofs, rear additions, and dormer sections that cannot take shingles get a rubber membrane instead. We install .060 EPDM.
Storm and Tree Damage. Winchester's mature trees are beautiful and they are hard on roofs. Limb strikes, wind damage, and what a nor'easter leaves behind.
Gutters and Skylights. New gutters and downspouts, plus VELUX skylight installation and replacement.
Roofing Winchester's Larger, Older Homes
The roofs on these houses are rarely one simple surface. You get multiple planes meeting at odd angles, dormers, valleys that run into other valleys, and almost always a low-slope section somewhere off the back where a porch or an addition was built. Every one of those meeting points is a place water can get in, and that is where the leaks we get called about actually start. Not out in the open field of shingles.
The flat-to-pitched transition is the one to watch. Shingles do not work on a low-slope roof, so that section needs a rubber membrane, and the two systems have to be tied together and flashed properly where they meet. Done right it is not a problem. Done fast it leaks within a few years, and the homeowner usually blames the shingles when the failure is at the transition.
Tree canopy is the other Winchester constant. Shaded slopes hold moss and stay damp, gutters pack with leaves twice a year, and gutters full of leaves in January are one of the main reasons ice dams form and push water back up under the roofing. A lot of what we get called about in this town traces back to water not leaving the roof rather than to the roofing itself. When we replace a roof we deal with ventilation and ice and water shield at the eaves, because that is what actually stops the problem coming back.
Underneath, older houses were sheathed with plank boards rather than plywood. Once the old roof comes off you sometimes find boards split, cupped, or spaced too wide to hold a nail properly, and new shingles over bad boards is a roof that fails early. We check the decking before anything new goes down, and we tell you up front what happens to the price if we find bad wood, so it is not a surprise on day two.
On a house like this the shingle you pick matters. A heavy architectural shingle has depth and a shadow line that looks right on an older Winchester home, where a thin three-tab reads flat and cheap from the street. We will show you what the real options look like on a house like yours rather than handing you a brochure and letting you guess.
Why Winchester Homeowners Choose Mark Brady Roofing
- 40 years on New England roofs, since 1986, including older homes with complicated rooflines.
- Owner run. Mark Brady and Glen Curtis inspect the roof, write the estimate, and are on the job.
- Shingle and flat roofs. Most Winchester houses need both on the same job, and we do them together rather than leaving you to coordinate two contractors.
- Repair before replacement. If your roof has good years left, we say so instead of selling you a tear-off.
- Certified installer. GAF Master Elite, Owens Corning Preferred, and CertainTeed certified, which means stronger manufacturer warranty coverage.
- Licensed and insured. Massachusetts HIC Registration #(781) 324-4312.
Common Roofing Questions in Winchester
My porch roof is flat and the main roof is pitched. Can you do both?
Yes, and that combination is on a lot of Winchester houses. The low-slope section gets a rubber membrane because shingles will not hold on that pitch, the main roof gets shingles, and the two get tied together and flashed at the transition. Doing both at once costs less than doing them in separate visits.
Do you work on slate roofs?
No. Slate is specialty work and it is not what we do, so if your Winchester home still has an original slate roof we are not the right call and we will tell you that on the phone rather than waste your time. We install asphalt shingle and flat roofing systems, and that is what we are good at.
Why does moss keep growing on my roof?
Shade and moisture. Winchester's tree cover keeps north-facing slopes damp, and moss holds that moisture against the roofing. It is more than cosmetic, because a roof that stays wet ages faster. Trimming back overhanging limbs and keeping the gutters clear does more than any product you spray on.
Do I need a permit to replace a roof in Winchester?
Yes, a roof replacement requires a building permit from the town, and we pull it as part of the job. Massachusetts also requires the contractor to hold HIC registration, and ours is #105477. Ask any roofer you are considering for their registration number and proof of insurance.
How long does a roof replacement take on a larger home?
If your Winchester roof needs attention, start with a free estimate. Call Mark Brady Roofing, we will get up there and look it over, and you will get a straight answer about whether it needs a repair or a replacement.
FREE ESTIMATES · NO PRESSURE
Get a Free Estimate in Winchester
If your Winchester roof needs attention, start with a free estimate. Call Mark Brady Roofing,
we will get up there and look it over, and you will get a straight answer about whether it needs
a repair or a replacement.

