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Typical Greater Boston range for this kind of work, from regional averages — not a quote from Dicky Matos. Use it to sanity-check bids, then get the real number in writing.
A square is 100 sq ft of roof surface — bigger than the floor plan because of pitch and overhangs.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
A recent customer who met Dicky at a home show said he emailed a price right away, then came out and confirmed it; after the job, a neighbor saw the work and signed up to have his roof done too. Dicky Matos is a roofing company that names Holyoke as its service area and says it has 19 years in business. Its Massachusetts home improvement contractor registration, number 198417, is active on the state registry, held by Dicky Matos Roofing, Inc. A recent customer described a complete tear-down and replacement that included replacing over 67 pieces of plywood, and said they hired him back to add seamless gutters. A 2026 customer said Dicky, Derek and his team removed slate from an old Victorian and put on a new asphalt shingle roof and a new skylight in two days. A 2024 customer said their roof was completed within 2 days and that the yard looked better afterward because of the clean up. In 2015, a customer whose house was hit by a falling tree said Dicky called back within 10 minutes, came to give an estimate a half hour later, and fixed the roof in half a day the next day. A recent Reddit commenter in r/northampton warned that they did not reseal around skylights and chimneys, so there were leaks, and "charged a fortune" to spend 20 minutes caulking them later. A 2024 HomeAdvisor reviewer wrote that the roof leaked for 6 years and that calls got only "lip service." A 2017 customer said a roof he re-shingled was later found not up to code because it was placed over too many layers, and that he never pulled a permit.
“avoid Dicky Matos. They didn't reseal around skylights, chimneys so there were leaks, and charged a fortune to spend 20 minutes caulking them later.”
Met Dicky at home show. He emailed me a price right away, site unseen. I asked him to come out, which he did, and verified the price he sent. Was significantly better price than others, so I checked references and everything looked good. Job went perfect, no problems. My neighbor saw the work and signed up to have his roof done as well. Also had my mother’s garage roof done. Highest recommendation.
I found Dicky Matos after numerous friends recommended him, I had a bunch of estimates for a new roof and Dicky gave the best price and had the best material. He even had someone who was able to build my dormer for my porch!! Talk about a package deal! The entire crew from start to finish which included replacing over 67 pieces of plywood, my roof was a complete tear down & replacement. I was so satisfied with the price I hired him back recently to add seamless gutters to complete the roof. If I could give more stars 🌟 I would. His crew were professional and cleaned up everything. I have included some before and after pictures 📸
Dicky, Derek and his team did an awesome job. It is an old Victorian that needed slate removed, a new asphalt shinged roof and a new skylight. All in two days. Good price and great work. Thank you.
Dicky Matos Roofing just completed a new roof on our 1793 farm house. This isn’t just our family home but a piece of our family farm, Little Pond Farm. We couldn’t be happier with the results! The process overall was extremely professional, efficient, clean, a great price and over all a fantastic service. We were impressed with how fast we were able to get a quote. They not only have all the right equipment but more importantly they have people who know how to use it!
We had needed a roof for a very long time, but were anxious to pull the trigger on it because of the cost. But DMR roofing made it painless, easy, and the quality of work was impeccable. Our roof was completed within 2 days, and the crew was amazing. They were efficient, polite and our yard actually looks better than it did before they came because of the amount of care they took in their clean up. I would HIGHLY recommend DMR for any roofing needs you may have!
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2 changes recorded — last scanned Oct 1, 2026.