Affordable Roofing Solutions in Middleborough, MA

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Lifetime Labor Roofing Warranty 

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View Our Interactive Job History Map

From roof replacements in Middleborough to seamless gutter installs in Carver, our map displays a proven track record across Massachusetts. Cycle Carpentry is known for detail-focused craftsmanship, reliable timelines, and professional service. Search the map by location or service type to see how we’ve helped homeowners like you.

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Qualified Roofer in Middleborough, MA

Middleborough, MA, is a historic town in Plymouth County known for its rich heritage and natural beauty. Established in 1669, it boasts landmarks like the Middleborough Center Historic District, featuring the town hall and numerous 19th-century buildings, and the Oliver Mill Park, showcasing remnants of 18th-century industrial mills along the Nemasket River. Residents and visitors enjoy recreational spots such as the Rocky Gutter Wildlife Management Area and the Soule Homestead Education Center, offering outdoor activities and educational programs.


Cycle Carpentry is proud to serve the Middleborough community, offering expert roofing, 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.​

Middleborough's Reliable Roofers

When it comes to roofing, shortcuts cost you more in the long run. Cycle Carpentry has delivered durable roof installs and replacements across Middleborough, MA for over 40 years. Our expert roofers use high-quality materials and time-tested techniques to build roofs that stand up to New England’s worst—from snow to summer heat—backed by a 10-year workmanship warranty.


Whether you need a new roof, storm damage repair, or preventative maintenance, we bring precision and professionalism to every job. Our team is fully licensed and insured, and we treat every roof like it’s our own. From start to finish, your home gets the attention it deserves.

Expert Siding Installation and Repair in Middleborough, MA

Siding shouldn’t just look good—it should protect your biggest investment. At Cycle Carpentry, we install fiber cement, composite, and premium vinyl siding built to last decades. Our siding solutions boost curb appeal while shielding your home from harsh weather, mold, and moisture. Every job is tailored to your style, needs, and budget.


If your siding is damaged, faded, or outdated, we can help. Our teamoffers seamless siding repairs that match existing materials and reinforce your home’s structure. With over 40 years of experience, we know how to do it right the first time—without mess or missed deadlines.

A Name Middleborough Homeowners Trust

Cycle Carpentry has earned a loyal following in Middleborough, MA by sticking to old-school values: honest work, quality materials, and treating your home with respect. We don’t overpromise—we overdeliver. And we back everything with a 10-year warranty for peace of mind.


We’re not a franchise or fly-by-night outfit. We’re a local team of licensed, insured pros who live and work in your community. Whether it’s roofing, siding, gutters or repairs, we build lasting relationships just like we build homes—with integrity, craftsmanship, and care.

Expert Roofing and Siding Installs in Middleborough, MA
Expert Roofing and Siding Installs in Middleborough, MA
Expert Roofing and Siding Installs in Middleborough, MA
Expert Roofing and Siding Installs in Middleborough, MA

Free Consultations!

We can return your quote within a few hours.

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We loved our experience with cycle carpentry! We are a military family, Our son was just deployed and Matt and Curtis were so patient with us! I loved their attention to detail! I highly recommend them to anyone needing roofing and siding!

- Rhonda Masterson via Google

Cycle is a joy to work with! They gave me an in depth walkaround of my house and told me exactly what my roof needed, and scheduling was a breeze. Their crew was professional and made sure everything was cleaned up after they were done!

- Aaron Maynard via Google

Residential Roofing

We're your Middleborough 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?

Did you know Middleboro is considered the “Cranberry Capital of the World”? Cranberry farming has shaped Middleboro’s economy and landscape for generations. Homes near bogs and wetlands often face higher moisture exposure, making durable roofing, weatherproof siding, and proper drainage systems essential for long-term property protection.