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 Len Gibely Contracting. 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.
Site cleanup — reviewers cite nail sweeps and daily tidying
Fixes others' work — repaired badly installed rubber roofs and failed siding
Thorough quoting — a 2025 quote caught boards competitors had missed
Verified registration — Massachusetts home improvement contractor licence active
BBB accredited — A+ grade and accredited status
Scope can grow — crews flag gable and board work beyond the quote
Exterior specialist — described work is roofs, siding, windows, decks and porches
One hundred and fifty Google ratings, every one of them a five. That is the headline for Len Gibely Contracting, and reading the written accounts the reason isn't mysterious: they do roofs, they do them fast, and they leave nothing behind. A May 2026 customer had the whole job done in one day — asphalt and rubber, plus repair work — with the area protected and the debris kept to a single spot. Another that same month put it more bluntly: "I haven't found any nails yet either."
Brian Dobbins owns the Peabody company. Deb runs the office, Reid writes quotes, and the crew chiefs get named by customers too. Its Massachusetts home improvement contractor registration is active, and it is BBB accredited with an A+.
Roofing is the bulk of the work and it comes in every variety: 30-year-old asphalt, cedar shake, flat rubber, CertainTeed systems, skylights, gutters and soffits. A November 2025 customer had rubber roofs another contractor had installed badly enough to leak; Gibely fixed them, then swept the driveway for nails and screws. That December, someone had two large and two smaller flat rubber roofs replaced in two days. And in May 2026 a second-time client said Gibely had done their roof more than 15 years earlier and came back to repair what a solar-panel company had damaged.
The rest of the outside of the house gets the same crew. In May 2026 a homeowner had the entire exterior shell of a house and a detached barn redone — siding, trim, windows, roof, a rebuilt sill, some framing, and a new deck, all in low-maintenance Azek and Hardie. A March 2026 client had every window in the house replaced. A March 2025 customer swapped out 30-year-old windows and a front entry door, and had the house checked for wood rot, which turned up clapboards and trim needing correction before a paint job. Decks and porches run right through: a screened porch and deck in October 2025, and a deck the same month where Brian called to ask which side the ADA rail should go on.
Two things worth knowing about how they quote. In December 2025 a customer said Reid's quote flagged boards that other companies had missed, and came with a long list of references. In April 2026 a crew chief pointed out gable work that wasn't on the original quote. Both read as thoroughness rather than upselling — but plan for a scope that can grow once the crew is up there.
Price lands well in the accounts too: a May 2026 deck client said the quote came in a full $10,000 under two other local companies. For a roof, siding, windows, gutters, a deck or a porch on the North Shore, this is about as consistent a record as you will find — 26 written accounts in the past six months alone, not one of them negative.
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Most recent comments
5.0Jun 16, 2026
We had a great experience with Len Gibely and with Brian Dobbins right from the get go. We had a huge bay window that needed replacement. The old window was constructed as a bay window but was put together from 3 parts. Now we actually have a real humungous bay window. Carpenters that work there are amazing, just a different level, from covering everything inside and outside to how they worked and cleanup just a pleasure to see. Ended up we had rotted siding around the window as well and we got that replaced as well. Overall price was very reasonable and it was done quickly. The teamwork there I have never seen before from cleanup crews to carpenters to siding and roofing is like I said a whole different level. We will definitely hire them again.
Had a great experience from roof quote to completion of roof replacement. Everyone I interfaced with was informative, responsive and professional. The crew on-site were productive and considerate with my concern regarding landscape. Little details regarding ice dam concerns were addressed and had the chimney re flashed which looks awesome. No damage to plantings and clean up was excellent. I am happy to recommend Len Gibley for your project.
Len Gibely Contracting recently replaced our 30 year old roof and did a great job! They were fast, efficient, respectful and it looks fantastic. Would definitely recommend them to anyone needing a roof replacement.
The team at Len Gibley Was wonderful they were kind courteous efficient on time can’t say enough good things about the whole crew. And the roof looks amazing!
Len Gibley Contracting recently completed a full renovation of the exterior shell of the house and detached barn. We replaced the siding, trim windows, roof, rebuilt the sill, some framing and constructed a new deck. All low maintenance materials, including Azek Trim, Hardie Board siding, metal roof, composite deck and railings. Brian and his crews were professional and courteous. All communication and responses to questions were timely and helpful. I can recommend them without hesitation.
RoofingWindows / Siding / GuttersCarpentryroof replacementsiding installationwindow replacementdeck building
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General Contractor / Remodelingflat rubber roofingcedar shake roofingskylight installationgutter installationporch constructionclapboard and trim repair