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 Kelly Roofing. 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.
Single-day replacements — reviewers describe full roofs finished in one day
Skylight work — 2025 review cites two remote-controlled skylights installed
Storm response — 2022 nor'easter repair started ahead of estimate
Registry-verified HIC — active MA registration held in the company's own name
Fair pricing — several reviews call estimates reasonable and honest
Site clean-up — homeowners repeatedly describe spotless finishes
One listed employee — BBB profile records a single-person business
By-appointment only — the company's own site states no set hours
Thin review volume — six reviews on file across five years
No recent jobs — newest described work dates to late 2024
Kelly Roofing, Inc. is a small Cape Cod roofing outfit run by Oliver M. Kelly, working out of Yarmouth Port and listed at 503 MA-28 in West Yarmouth. Its own site describes a by-appointment-only, locally owned and operated business, and the Better Business Bureau records the company as started in 2001 and incorporated in 2014, with one employee and Mr. Oliver M Kelly as president.
The credential picture is unusually clean for a one-man shop. Massachusetts' state registry verifies an active Home Improvement Contractor registration, number 216218, held of record by Kelly Roofing Inc — the registry holder matches the business name. The BBB has accredited the company since January 2020 and grades it A+, though that profile publishes no star rating and no review bodies of its own.
What homeowners describe is consistent and specific rather than generic. A February 2025 reviewer wrote that Oliver and his team replaced a full roof with new venting and two remote-controlled skylights in a single day the previous November, calling the estimate responsive, the price reasonable and the clean-up excellent. A 2023 review described the removal of an old cedar-shingled roof on a 200-year-old house and a switch to architectural asphalt that the owner felt improved the curb appeal, and a January 2022 review described an emergency after a nor'easter tore off part of a roof, with the crew arriving a day ahead of the estimate and the owner on site throughout. A Cape Cod Reddit commenter in May 2024 reported they could not recommend Kelly roofing enough — a mention-only signal, attributed rather than asserted.
What is thin is volume, not quality. The file holds six reviews spanning 2021 to 2025 and Google publishes a 4.9 average from 15 ratings, so this is a small, consistently well-reviewed record rather than a deep one, and nothing on file describes a job in the last six months. Worth confirming directly: that the HIC registration is still current at the time you sign, what the by-appointment scheduling means for your timeline, and — since the BBB file lists a single employee — who exactly will be on your roof.
Kelly Roofing is a sensible call for a Cape homeowner wanting a straightforward roof replacement, repair, skylight or gutter job from a registered owner-operator, provided you are comfortable hiring on a short, strong track record rather than a large one.
Heard around town
On Reddit
I live in Dennis and I am looking for recommendations on roofing companies. I need a new roof and also some leak repair around the chimney siding.May 2, 2024
I live in Dennis and I am looking for recommendations on roofing companies. I need a new roof and also some leak repair around the chimney siding.May 2, 2024
Oliver and his team replaced our full roof, with new venting, and 2 remote controlled skylight windows in one day last Nov (2024). Very responsive with estimate and very reasonable price. Quality work done. Excellent clean up. Highly recommend.
Oliver and his crew are amazing. They did excellent quality work on our 200-year old home. We thought the removal of the old cedar wood shingled roof would also remove a lot of the charm, however with Olivers guidance and efforts, we seem to have upgraded the curb appeal with our architectural asphalt roof. Highly recommend the ‘Driftwood’ Max Def shingle.
I can’t thank Oliver enough for his patience and attitude throughout the process. He is a personable, kind and hardworking person who shows up for the job. His install team all worked hard and very effeciently. Major bonus points for navigating the multiple yard projects happening and not making a mess or damaging plants in the garden. Oliver roofing deserves your business.
Did our roof. Neighbors were so impressed with the speed and workmanship of his crew hired Kellys to do their roof. Many of our clients and friends have used him to replace their roofs. All very happy. Very reasonable, Honest and professional!
We were in a bind after a Nor’easter blew a section of our roof off in late October. We ended up talking with several roofers but chose Oliver because of how responsive he was and because we felt his price was fair. He and his hard-working crew got right to it. They were on site a day before Oliver had originally estimated, which was great news to us. He was on site throughout the entire time, over seeing things. The finished product looks great. I wholeheartedly recommend Kelly Roofing. If I could give them 10 stars, I would!