Experienced Roofing Contractors in Rockland, MA

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Work We're Proud of - Near You

Want to see the difference we’ve made across Massachusetts? Our job map features completed roofing, siding, and gutter projects in towns near you. It’s a transparent look at our quality, consistency, and local commitment — one home at a time. Check out our work and see why neighbors keep recommending Cycle Carpentry.

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Trusted Roofers in Rockland, MA

Rockland, MA, is a town rich in history and community spirit. Established in 1874, it was once a hub for shoe manufacturing, with landmarks like the Emerson Shoe Company building reflecting its industrial past. Today, Rockland boasts attractions such as the Rockland Memorial Library and the Lower Union Street Historic District, showcasing well-preserved architecture from the 18th and 19th centuries. ​



Cycle Carpentry is proud to serve the Rockland community, offering expert roofing, siding, James Hardie 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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You Found the Roofing Contractors Rockland, MA Recommends

Choosing the right roofer shouldn’t feel like a gamble—it’s about trust, skill, and proven results. At Cycle Carpentry, I’ve been helping Rockland, MA homeowners protect their homes with durable roofing systems built to withstand New England weather.


From leak repairs and full roof replacements to gutter installations and siding upgrades, I offer honest service backed by 40+ years of experience. Take a look at my past work, read the reviews, and let’s talk about how I can bring lasting value to your home.

Questions You Should Ask Your Roofing Contractors

Not all roofers are created equal—and the right questions can save you thousands. When you're preparing for a roof replacement, leak repair, or full exterior renovation, it’s crucial to go beyond price and credentials. Asking the right questions helps you avoid delays, confusion, and surprise costs—and ensures your roofing project goes off without a hitch.


Before hiring a roofing contractor in Rockland, MA (or anywhere in southeastern Massachusetts), be sure to ask:


  • How will you access my roof?
    Knowing how your contractor plans to access your roof allows you to clear space and prevent property damage during the job.
  • What is the estimated project start and completion date?
    Get a clear timeline so you can prepare your home and schedule accordingly—especially if you're coordinating other services like siding or gutter installations.
  • Who is my main point of contact throughout the project?
    Whether it’s about materials, scheduling, or concerns mid-project, direct communication builds trust and avoids misunderstandings.
  • What’s included in the roofing estimate?
    Clarify if the quote covers tear-off, disposal of old shingles, underlayment, flashing, ridge vents, and labor—transparency here helps avoid hidden fees.
  • What type of roofing materials do you recommend and why?
    Ask about the best shingle brands, underlayment, or gutter guards for your specific roof pitch, sun exposure, and regional weather.
  • Is your work covered by a labor warranty?
    At Cycle Carpentry, I offer a 10-year labor warranty because I believe you deserve peace of mind long after the job is done.
  • How do you handle unforeseen issues like rotten decking or structural repairs?
    Uncovering damage mid-project is common—so ask how those situations are handled and priced before signing.
  • What’s your preferred payment schedule and accepted methods?
    Clear payment terms eliminate last-minute surprises and help you plan your budget confidently.


When you’re investing in your home’s roof, asking these smart, specific questions ensures your project stays on time, on budget, and done right—the first time. And when you’re ready, Cycle Carpentry is just a call away for honest, experienced roofing services in Rockland and surrounding towns.

Roofing Built for New England


A roof isn’t just shelter—it’s year-round protection from everything Massachusetts weather throws your way. At Cycle Carpentry, our roofers specialize in roofing services designed specifically for New England homes. From asphalt shingles to complete roof replacements, our expert roofers in Rockland, MA deliver long-lasting, dependable solutions backed by over 40 years of hands-on experience.


Whether you’re upgrading your home’s exterior with new siding, replacing gutters, or scheduling a seasonal gutter cleaning, we bring the same care, craftsmanship, and attention to detail to every project. We’re licensed, insured, and committed to treating your home like our own. Call today for a free quote and discover why Rockland homeowners trust Cycle Carpentry.

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Cycle Carpentry did a great job on my house. From the estimate to small details finishing the job, this was a great experience. My home looks fantastic and I’ll be having them back to do my roof in the future. I recommend Cycle Carpentry to anyone looking for siding on their home.

- David Michalak 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 B via Google

Residential Roofing


We're your Rockland Massachusetts residential roofing contractor! 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?

In the 19th and early 20th centuries, Rockland was known for its booming shoe factories. The town’s industrial roots still influence its character and architecture today.