What does a roof replacement cost in Greater Boston?
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Wicked Smart Exteriors. 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.
Same-week response — reviewers describe quotes within hours and starts within days
One-day reroofs — strip-and-reroof jobs finished in a single day
Thorough cleanup — no nails or debris left, furniture moved back
Owner on site — Ryan Dolan runs consultation through installation himself
Competitive bidding — homeowners chose them after three to five quotes
Active state registration — MA contractor registration 176332 verified in the registry
Scheduling reliability — one Google reviewer reported two last-minute reschedules without a call
Dated written record — twenty quoted accounts fall between 2018 and 2021
Wicked Smart Exteriors is a small roofing company run out of 68 Byam Road in Chelmsford by owner Ryan Dolan, whose name is the one on the company's Massachusetts home improvement contractor registration — number 176332, verified active in the state registry. It is hired mainly for one thing: stripping an old roof and putting a new one on, usually in a single day.
The written history runs from 2018 to 2026 and is unusually consistent. Google publishes 4.8 stars from 23 ratings; HomeAdvisor publishes 4.9 from 62. What people who hired the company describe over and over is speed. One 2024 reviewer said Dolan was at their house within hours of the first call for a quote and the crew was on time both days. Another, after a roof leak in 2023, had work starting the next morning.
Cleanup comes up almost as often as the roofing itself. A 2022 customer watched a stripped roof, a new ridge vent and gutter pipes all go in inside eight hours, and noted the crew moved patio furniture out of the way and left the site as though they had never been there. A 2019 homeowner said no nails or roofing debris were left in the lawn.
Price shopping is a recurring theme too: several reviewers say they took three, four or five competing bids before choosing this company, and picked it on a mix of price and confidence rather than on being cheapest.
The work reaches past shingles. Homeowners describe seamless gutters installed after the old ones were replaced and the fascia painted, vinyl siding put back after a wind storm, solar skylights, chimney repointing alongside a roof job, and flashing repaired where squirrels had chewed the lead at a chimney line. A 2019 job on an 1878 Victorian in Lowell involved strengthening old roof boards and redesigning the attic ventilation — soffit and ridge vents replacing scoop vents — to free up roof space for solar panels, and included a commercial-grade rubber roof on the adjoining flat section.
The one dissenting account is a 2024 Google review rating the company one star: the writer says Dolan rescheduled once with under twelve hours' notice and again during the arrival window, without calling. Scheduling is the thing to pin down in writing. It is also worth knowing that twenty of the written accounts date from 2018 to 2021, so ask what the crew looks like now and what current lead times are.
For a straightforward asphalt shingle replacement, a leak repair, or gutters on the Chelmsford and Lowell side of Middlesex County, this is a credible small-shop choice with an owner who runs the job himself. Confirm registration 176332 with the state and get the start date in writing before you sign.
Heard around town
On Reddit
roofer recommendationsMay 14, 2026
“Wicked Smart Exteriors replaced my roof and did a great job. Small local company, you talk directly to the owner.”
Ryan Dolan was recommended to us by our realtor to replace our roof. From the beginning, Ryan's communication was excellent. He inspected our roof, provided us a quote, answered all our questions, and was very flexible in working with our scheduling timeline as we needed to coordinate with another company to remove and re-install our solar panels. Ryan's team was courteous and efficient. They replaced the large roof on our home in the estimated time and did an excellent cleanup job. Ryan identified some additional issues during the roof replacement and immediately provided a recommendation and quote to replace two old power fans. His team's ability to remove and dispose of obsolete structures from our roof (deck awning & various satellite dishes) complete all necessary repairs (chimney flashing, power fans, some rotted siding), and replace roof-mounted heating elements were all greatly appreciated. His team even accommodated a late re-schedule initiated by our solar panel crew. I would highly recommend Ryan's roofing services!
Ryan and his team at Wicked Smart Exteriors were recommended to me by a friend. From the moment Ryan came out to inspect my roof he was extremely professional and honest in his assessment of my roof. They put my new roof on in a day and were very thorough in their prep and clean-up of the job. I would highly recommend Ryan and Wicked Smart Exteriors for your next roofing job!!
Ryan’s crew did awesome thorough job replacing our roof and repointing our chimney about 5 yrs ago. Mason did superior work! Great communication over all and great clean up.
—-Ryan was most responsive when I called recently to having 2 huge pieces of rafting (vinyl siding) replaced that came down in wind storm, -when other contractor never returned my call!
-His crew went above and beyond when I asked them also to remove a little vinyl siding for me to remove a mouse nest. They took care of everything, including adding another corner piece of metal to cover opening (under vinyl siding) and caulked several places where there were openings.
Wicked Smart Exteriors is Most Responsive, team does a thorough job & clean up-and they go above and beyond to do things right!
I first met Ryan Dolan, owner of Wicked Smart Exteriors, when he came to my house to assess a ventilation issue in my attic. He didn’t charge me for the visit, even though it was unlikely to turn into a job. To confirm his assessment, he even sent one of his guys to evaluate my soffits, also at no charge. Ryan has an ease about him that immediately created trust. He also seems to have long-standing contractors and employees whose work is consistently high quality, which can be hard to find in this type of business.
I’d had replacing my gutters in the back of my mind for years, and when I found out he did that work, I asked for a quote. I’m usually someone who gets at least three quotes, but this time I didn’t bother. I found his price fair—both to me and to him. I also hired him to add more ventilation to my soffits.
Since Ryan runs a small business, schedule openings can sometimes come up last minute, even the evening before. I think it’s worth mentioning so future clients can proactively agree on timing and level of flexibility. For me, it worked out perfectly since I have a very flexible schedule and work from home.
After he replaced my gutters, I noticed some water dripping from behind them. When things don’t go right the first time, it can be stressful for a homeowner—there’s always that worry about whether a contractor will be defensive or avoid standing behind their work. Ryan was the opposite. He had his team out within a couple of days to fix the issue, then insisted we wait through a few rainfalls to be sure the problem was resolved. I also want to add that the men who work for him were great to have around—I felt completely comfortable with them at my home, which says a lot about the kind of business Ryan runs. I even felt comfortable paying him right away, but he pushed back and told me to hold off until I was certain everything was working properly.
Finding a contractor who is truly trustworthy feels like finding gold. I would highly recommend Ryan and Wicked Smart Exteriors to anyone needing roof, gutter, or related work.