Trusted Roofer in Milton, MA

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Lifetime Labor Roofing Warranty 

Financing Available

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Proof of Work, Not Just Promises

Cycle Carpentry’s project map is more than a portfolio—it’s a record of trust built one home at a time. Browse roofing jobs in Braintree, siding in Quincy, and gutter installs across Randolph. Our local experience is visible, searchable, and growing every day. See exactly what we’ve done—and where we’ve done it.

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Roofing, Siding, and Gutters Milton Can Count On

Cycle Carpentry delivers full exterior solutions for Milton, MA homeowners, expert roofing, precision-installed vinyl and fiber cement siding, and high-performance gutters. We handle everything from minor repairs to full replacements, all backed by over 40 years of experience. Licensed, insured, and locally trusted, we combine quality craftsmanship with responsive service to protect your home and elevate its curb appeal—no shortcuts, just results.

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Roof Replacements and Repairs Done Right

Your roof is your home’s first line of defense, and we treat it that way. Whether you're facing storm damage, aging shingles, or leaks, our roofing team in Milton, MA delivers professional roof repair and replacement services with premium materials and a 10-year workmanship guarantee. We specialize in asphalt, rubber, and composite systems built for New England weather and long-term peace of mind.

Vinyl and Fiber Cement Siding Experts

Upgrade your home’s appearance and protection with low-maintenance vinyl siding or durable, weather-resistant fiber cement siding. Milton homeowners rely on Cycle Carpentry for expert siding installation, repair, and full-home transformations. We help you choose the best material for your budget, energy needs, and style—then install it with craftsmanship that lasts. It’s more than siding—it’s a long-term investment in your home.

Seamless Gutters and Gutter Guard Installation

Old, leaky gutters can cause serious damage over time. We install seamless gutter systems and gutter guards designed to handle heavy rain and debris while protecting your roof, siding, and foundation. Cycle Carpentry offers gutter installation and replacement services in Milton that prioritize performance, drainage, and aesthetics—keeping your home safe, dry, and ready for New England’s unpredictable storms.

Milton’s Trusted Exterior Home Contractor

Homeowners throughout Milton trust Cycle Carpentry because we show up, follow through, and stand behind our work. With hundreds of five-star reviews, full licensing, and decades of hands-on experience, we’ve earned our place as a reliable choice for roofing, James Hardie fiber cement siding, vinyl siding and gutter replacement. We don’t do flashy sales—just honest service, clean job sites, and results that speak for themselves.

Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
Home Improvement Contractors in Milton, MA
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Free Consultations!

We can return your quote within a few hours.

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I personally highly recommend Curtis and his Crew, Cycle carpentry Is constantly putting out good quality work with compassion for the homeowner and his business. It’s always an absolute great experience dealing with them.. highly recommend.

- Chris Ballard via Google

Curtis from Cycle Carpentry is the best choice for all your roofing needs! I texted him requesting a quote and he showed up within a few days and emailed me what it would cost in a timely manner. Once I agreed to the work to replace the entire roof of a ranch home, he said it would be done in one day! Boy, I was so impressed by his promptness and the professionalism of him and his guys. We even have a small dog that runs the backyard and we asked him to make sure no nails where left behind, he made sure of it with his fancy magnet machine. I never found a nail after he left, front or back of the home. He is fair, honest and won't take you for a ride just to capitalize on his business gains.

- Jonathan H via Google

Residential Roofing

We're your Milton 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 Milton 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 Milton, MA is home to the Blue Hills Reservation, offering over 7,000 acres of hiking trails and scenic views just minutes from Boston? This historic town blends natural beauty with colonial charm, making it one of Massachusetts’ most desirable places to live—and renovate.