Verified record
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.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
Wicked Smart Exteriors is a Chelmsford roofing outfit run by owner Ryan Dolan, and the thing that shows up again and again across eight years of reviews is Dolan himself — homeowners talk about him personally inspecting the roof, explaining the options, and staying reachable through the job. HomeAdvisor puts the company at 4.9★ across 62 ratings and Google at 4.8★ across 23; the state home improvement contractor license tied to Dolan is active. The written record is long and consistent. A 2019 review described a complex project on a circa-1878 Victorian in Lowell — a traditional sloped roof plus an adjoining flat roof, with the old roof boards strengthened and the attic ventilation redesigned to free up space for a solar array that followed. A 2022 review described the company replacing a leaking roof, rotted trim, and missing gutters left behind by a prior installer's bad work. More recently, a September 2025 review recalled Dolan making two free visits — one to assess a ventilation issue, a second to have a crew member evaluate the soffits — neither of which turned into a paid job at the time. Reviewers across the years describe him going past the original scope: a November 2025 review described him responding quickly to storm-damaged vinyl siding and removing a section to clear a mouse nest, years after the original roof and chimney repointing job. Recent activity, including two reviews in the last six months, continues the same pattern — thorough inspections, flexible scheduling around other trades, and clean job sites. Not every account is spotless. In an October 2024 review, one customer described being rescheduled twice with little or no notice on a project they'd told Dolan was time-sensitive, and said calls afterward went unanswered — a sharp contrast to the responsiveness most other reviewers describe. For a full roof replacement or a repair with some complexity — old materials, ventilation problems, coordination with another trade — Wicked Smart Exteriors has a long paper trail to back it up; the one sour review is worth keeping in mind if timing is critical.
“Wicked Smart Exteriors replaced my roof and did a great job. Small local company, you talk directly to the owner.”
“Wicked Smart Exteriors (R. Dolan, Chelmsford) did our house this year. They do repairs and whole roof replacements and I was very impressed.”
Ryan and his team were quick, reliable, and all around great to work with. We will definitely recommend them to friends in need of a new roof.
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.
Specializes in
Also offers
Languages
1 change recorded — last scanned Aug 16, 2026.
Design-build additions3.8
Solar ownership or power purchase agreements2.9