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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.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
Oliver Kelly is the name Cape Codders give when someone on r/CapeCod asks for a roofer — four times since 2023, once this July as "best around" — and the Google reviews are about him personally: on site the whole job, responsive on the estimate, priced fairly. Kelly Roofing is a one-man-run Yarmouth Port company (Oliver Kelly is president; the BBB file dates the business to 2001 and its incorporation to 2014) doing roof replacement and repair, skylights, roof cleaning and gutters, by appointment. Its Massachusetts home improvement contractor registration is active on the state registry, and the BBB grades it A+ with accreditation since 2020. The reviews are few — six on Google, 2021 to 2025, all five stars — but specific. A February 2025 reviewer had a full roof, new venting and two remote-controlled skylights done in a single day the previous November. In 2023 a 200-year-old house lost its cedar shingles for an architectural asphalt roof and the owner felt the curb appeal went up, crediting Oliver's guidance. A January 2022 customer whose roof section blew off in an October nor'easter chose him for responsiveness and price and had the crew on site a day earlier than promised, with Oliver overseeing throughout. Two others describe tear-off and re-roof in one day and a spotless clean-up, and one says neighbors hired him after watching the crew work. A good call for a Mid-Cape roof replacement or storm repair when you want the owner on the roof. Ask how far ahead he is booking, since it is appointment-only and a small crew.
“Kelly Roofing. Best around”
“Can't recommend Kelly roofing enough”
“Yport Oliver Kelly”
“Kelly roofing”
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.
Great prices and great work!
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!
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1 change recorded — last scanned Aug 16, 2026.
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