
RESIDENTIAL & COMMERCIAL ROOFING


WHAT OUR CUSTOMERS SAY
Verbatim Google reviews from real Winter Hill customers.
MEET THE FOUNDER

Gustavo Cardoso and Robert have been working together since 2010, building their careers from the ground up as roofing installers before becoming trusted leaders in the industry. Their hands-on experience and dedication to quality have helped establish Winter Hill as one of the area's most trusted roofing companies, serving homeowners and businesses across Boston's North Shore and northwest suburbs.
GAF Master Elite certified, fully licensed and insured, and run the same way on every project: daily updates, a written contract, a crew that finishes on schedule, and a site left cleaner than we found it.
To be the roofing company homeowners and businesses recommend to their neighbors. The one people call when the work has to be right, on time, and backed in writing.
Manufacturer-grade materials, honest written quotes, daily communication, on-schedule builds, and a spotless cleanup. One company accountable for every roof we touch.


WHAT WE DO
Roof repair, replacement, and new installation, commercial flat and low-slope systems, plus siding and gutters. Installed as complete manufacturer-grade systems, detailed for New England weather and backed in writing.
WHY HOMEOWNERS AND BUSINESSES PICK US

Most roofers install the system and move on. We run the whole job the right way: GAF Master Elite installation, a written contract, daily updates so you always know where things stand, an on-schedule build, and a spotless cleanup that leaves your property better than we found it. Every roof is backed by manufacturer warranties.

OUR WORK
A sample of Twin Cities commercial and industrial flat-roof work.
Click any photo to see the detail.



Our Process
Free inspection. Honest written assessment and quote. Manufacturer-grade materials. Precision install. Final walkthrough and warranty. Each step explained, documented, and on your timeline.
Reach out by phone or our online form. We get back to you to schedule a convenient time to come out.
A member of our team visits to look at the project, take measurements, and understand exactly what you need.
We send a clear, itemized proposal within a day or two, then follow up to answer every question, no pressure.
Once you approve the proposal, we pull any permits needed and stay in touch until we lock in your start date.
Our crew completes the work on schedule, keeps you updated throughout, and leaves your property spotless.
You are in control at every step. No pressure, no obligation, no surprise charges.
OUR PROMISE
A free, photo-documented roof inspection from a GAF Master Elite contractor, and a complete roofing system that qualifies for the strongest manufacturer warranties available.


KNOWLEDGE & ADVICE
GAF systems, ice and water shield, attic ventilation, storm damage, and commercial roofing. Plain-spoken guidance from a local roofer.

Learn to spot roofing scams in Danvers before signing anything. A local GAF Master Elite roofer breaks down 5 red flags homeowners miss.
Read More ›
Fewer than three percent of roofers earn the GAF Master Elite rating. Here is what it means for the system on your home and the warranty behind it.
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Two details decide whether a North Shore roof lasts its full life or fails early: balanced attic ventilation and ice and water shield. Here is why.
Read More ›QUESTIONS
We serve Boston's North Shore and northwest suburbs, including Andover, North Andover, Boxford, Lynnfield, Topsfield, Middleton, South Hamilton, Concord, Chelmsford, Burlington, Reading, Wakefield, Winchester, Lexington, and the surrounding towns. Not sure if you are in our area? Give us a call.
GAF Master Elite is the highest contractor certification GAF awards, and fewer than three percent of roofers in North America hold it. It means we are factory-trained, properly licensed and insured, and able to install complete GAF systems that qualify for the strongest manufacturer warranties available.
Architectural asphalt shingle, standing-seam metal, natural and synthetic slate, and flat membrane systems (EPDM and TPO) for low-slope and commercial roofs. We install each as a complete system and help you pick the right one for your property and budget.
Yes. As a GAF Master Elite contractor, the systems we install qualify for manufacturer-backed warranties on both the materials and our workmanship. You get the warranty terms in writing before the job starts.
Yes. Winter Hill is fully licensed and insured, holding Massachusetts HIC #204047 and CSL #CS-118689. We pull the permits for your project and provide current documentation on request.
Most residential roof replacements are completed in one to three days depending on size, pitch, and weather. Larger or flat-roof projects can run longer. We give you a clear schedule up front, keep you updated daily, and finish on time.
Yes. We install and repair commercial flat and low-slope systems, including TPO, EPDM rubber, and roll roofing, for businesses and property owners across the North Shore and Greater Boston. Call us to set up a site visit and a written proposal.
Yes. We work with Hearth to offer flexible monthly payment plans on roofing and exterior projects. Checking your options takes minutes and lets you pick a plan that fits your budget. Ask us about it during your free estimate.

READY TO START?
Tell us about your roofing project, residential or commercial. A GAF Master Elite team will inspect it, show you what we find, and give you an honest written quote. On schedule, in writing, no pressure.
We will never send you spam. No obligation. No pressure.
WHERE WE WORK
Andover, North Andover, Boxford, Lynnfield, Topsfield, Middleton, South Hamilton, Concord, Chelmsford, Burlington, Reading, Wakefield, Winchester, Lexington, and the surrounding towns. Free inspections across the service area.