Expert Roofing Contractors in Winchester, MA

A roof replacement is one of the larger home improvement investments you'll make. For Winchester homeowners, it's also an opportunity to address problems that have been developing for years. Maybe you've dealt with ice dams every February. Maybe there's a persistent leak around a dormer that patch repairs haven't fixed. Maybe the previous roof was installed over old layers, and it's time to strip everything down and start fresh with proper underlayment and ventilation.

Massachusetts weather is hard on roofs. The freeze-thaw cycle from December through March creates real stress on roofing materials. Temperatures swing above and below freezing repeatedly, sometimes within a single day. That expansion and contraction cracks shingles, stresses flashing, and opens gaps where water gets in. Ice dams form when heat escapes through the attic, melts snow on the roof deck, and that meltwater refreezes at the cold eaves. Prevention requires proper attic ventilation, adequate insulation, and ice and water shield membrane at vulnerable points.

Winchester's architectural character adds complexity. The Queen Anne, Shingle Style, Colonial Revival, and Tudor Revival homes that define neighborhoods like Wedgemere have rooflines that are anything but simple. Steep pitches, multiple dormers, hand-cut valleys, and decorative elements all require precision work. For homes in the town's historic districts, the Historical Commission may review exterior work, so material choices need to respect architectural character.

We install primarily architectural asphalt shingles from GAF, Owens Corning, and CertainTeed. Installed correctly with proper ventilation and ice and water shield, they'll give you 25-30 years of service. For a typical colonial in Winchester, expect $15,000 to $28,000 depending on size, pitch, and complexity. Larger Victorian homes with steep pitches and multiple dormers run higher, sometimes $30,000 to $40,000.

Metal roofing makes sense if you're staying long-term or have recurring ice dam problems. The upfront cost is roughly double asphalt, but metal roofs last 50+ years and shed snow instead of holding it, reducing ice dam risk. Standing seam metal can work within historic district guidelines when color and profile are chosen appropriately. For historic restoration, slate roofing lasts over a century but costs $15-30+ per square foot.

Our process starts with a thorough inspection. We get on the roof, check decking condition, evaluate flashings, and look at attic ventilation if accessible. Some roofs have years left with targeted repairs. Others need full replacement. We'll tell you honestly which situation you're facing. If replacement is right, you get a detailed written estimate with everything itemized.

We handle all permitting with Winchester's Building Department. The town uses an online permitting system. We submit the application, pay fees, and schedule inspections. The permit process typically adds a few business days before work starts. Once approved, most installations take 1-3 days depending on size and complexity. We protect landscaping during work and haul away all old materials.

You get two types of warranty coverage. Manufacturer warranties cover the materials, with GAF, Owens Corning, and CertainTeed offering limited lifetime warranties on architectural shingles. Our workmanship warranty covers installation quality. About 90% of premature roof failures come from installation issues, not defective materials. Poor flashing, inadequate ventilation, or incorrect nailing patterns cause problems that material warranties won't cover. Our written workmanship warranty addresses that gap.

We've been doing this work for 27 years under the same family ownership. When you call, you talk to someone who knows your project and can answer questions directly.