Roofing Contractors in Pembroke, MA

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Explore Our Local Project Map

See the neighborhoods we’ve worked in, the roofs we’ve replaced, and the siding we’ve installed with pride. Our interactive project map showcases the depth of our work and the trust we've earned in towns like Hanover, Pembroke, and East Bridgewater. This isn’t just a list of jobs — it’s a reflection of our reputation.

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Reliable Roofers Serving Pembroke, MA

Pembroke, MA, established in 1712, is a historic South Shore community known for its scenic ponds, rich shipbuilding heritage, and family-friendly neighborhoods. Cycle Carpentry is proud to serve the Pembroke community, offering expert roofing, JamesHardie fiber cement siding, vinyl siding and gutter services tailored to withstand Massachusetts' diverse weather conditions. As a trusted roofer in the area, we are committed to enhancing and protecting your home's exterior with quality craftsmanship and durable materials.​

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Leak-Free Roofing Guaranteed in Pembroke, MA



A leaky roof is never just a small problem—it’s a sign your home needs expert care. At Cycle Carpentry, our roofers provide reliable roof repairs and leak-proof roof replacements that protect your home and preserve its value in Pembroke, MA.


With over 40 years of experience, I specialize in affordable roof installations, flashing repairs, and weather-resistant roofing systems. Whether it’s storm damage or old shingles, I deliver prompt, professional service and lasting results—backed by honest estimates and a reputation you can trust.

Signs You Need Roof Services Immediately

Not all roofing problems announce themselves with a major leak—some signs are subtle but serious. Recognizing these red flags early can help you avoid expensive damage and protect your home’s structure. If you notice any of the following, it’s time to call Cycle Carpentry for a professional roofer inspection or repair service in Pembroke, MA.


Here are urgent signs your roof may need immediate attention:


  • Visible Sagging: A sagging roofline is never a minor issue. It often points to serious underlying structural damage, waterlogged decking, or inadequate support. This requires a roofing professional to assess and repair before further deterioration occurs.
  • Shingle Trouble: If you spot curled, cracked, dented, or missing shingles, your roof’s first line of defense is compromised. A few damaged shingles can often be repaired—but widespread damage usually signals it’s time for a full roof replacement.
  • Water Damage & Moisture Issues: Look for ceiling stains, mold growth, musty odors, and damp spots in the attic. These symptoms often indicate a roof leak, damaged flashing, or underlayment failure. Left untreated, moisture can lead to wood rot and costly structural problems.
  • Granule Loss: Check your gutters for granules from asphalt shingles. Excessive granule loss means your shingles are aging and no longer offering proper UV or weather protection.
  • Rising Energy Bills: A failing roof with poor insulation or ventilation can let heat escape in winter and trap it in summer—causing your HVAC system to work overtime and your energy bills to spike.


Don’t wait until small issues become major repairs. With over 40 years of hands-on experience, Cycle Carpentry delivers reliable roofing services—whether you need repairs, a roof replacement, or a detailed inspection. Contact me today for a free consultation and ensure your home stays safe, dry, and protected.

Contact the Roofing Contractors Pembroke, MA Prefers

Delaying roof repairs is one of the costliest mistakes a homeowner can make.
If you've noticed missing shingles, leaks, or sagging, it's time to act fast. The sooner you address these issues, the more likely you are to avoid extensive damage—and the expense of a full roof replacement.


At Cycle Carpentry, our roofers provide trusted roofing and siding services in Pembroke, MA. From detailed roof inspections and expert repairs to complete roof replacements, every project is handled with care and precision. We also offer vinyl siding installation, seamless gutter systems, and seasonal gutter cleaning—all backed by over 40 years of hands-on experience.


If you’re looking for a reliable, local contractor who treats your home like their own, call Cycle Carpentry today for a free quote. Let’s protect your home and boost its value—starting from the roof down.

Free Pembroke MA Roofing Consultations!

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I am very happy and will definitely use Cycle Carpentry again. I needed a new roof and chimney repointed, Curtis explained the job and how long it will take and the price was reasonable. Everyone was courteous and polite, they cleaned up all the debris and most importantly they were done in one day.

- Aulus Maloof via Google

Great experience working with Curtis, Elias and the team from Cycle. From the initial introduction to the final truck leaving the driveway they were awesome. The finished product came out fantastic. Highly recommend to anyone!

- Chris Riley via Google

Residential Roofing


We're your Pembroke Massachusetts residential roofing specialists! Call us for repairs, replacements, and new installations.

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Siding Installation


You can count on Cycle Carpentry for vinyl, cedar, and cement fiber siding installations. Quality siding makes your home look great.

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Gutters and Gutter Guards


Make sure rainwater and melting snow run out into your yard and not up against your walls. Call us for new gutters and gutter guards.

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Did You Know?

With features like Oldham Pond and Furnace Pond, Pembroke is a popular spot for lakeside living—making proper roofing, siding, and gutter systems especially important for managing moisture and seasonal weather.