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 Woodland HomeWorks. 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.
Quote accuracy — May 2026 customer said the final bill matched exactly
Winter ice dams — next-day scheduling reported in February 2026
Active registration — Massachusetts home improvement contractor licence verified
Pricing challenged — a January 2026 review called quotes nearly double competitors
Sales pressure claim — the same review warned about a high-pressure contract
147 Google ratings, a 5.0 average, and one word that keeps surfacing: clean. Woodland HomeWorks is an exterior contractor working out of Billerica — roofs first, then siding, gutters and skylights — and what customers describe over and over is a crew that shows up early, finishes fast, and leaves the yard the way it found it.
The speed isn't marketing. A colonial got a full reshingle in two days this April, and the homeowner's parting line was about the site cleanup. Later that month another customer had the crew on site at 8am each day, replacing siding alongside the roof and keeping them posted at each stage. In May, a customer's final bill came in exactly at the quote. And in February, when the ice dams came, one homeowner had them cleared the day after calling.
The names come up almost as often as the work: Tim on estimates, Aja in the office, Nick and Joe running the jobs. A December 2025 reviewer who redid an entire exterior — siding, roof, windows, doors, a porch extension and new skylights — listed all four. Bigger projects show up too: another 2025 customer described 60-year-old aluminum siding stripped off and replaced with CertainTeed Cedar Impressions vinyl, with the project managers stopping by daily.
The dissent is worth reading before you sign. In January 2026 one reviewer wrote that the company charges nearly double what other area roofers do, and warned against signing a high-pressure, inflated contract without getting several estimates first. That review doesn't dispute the workmanship — its quarrel is with price and the sales process, and it sits against a long run of customers who called the pricing fair or better. Two more quotes will tell you which of those you're looking at.
Its Massachusetts home improvement contractor registration is active, held by Woodland HomeWorks, LLC, and the BBB page shows an A+ with accreditation since July 2023. For a roof, siding, gutters or a mid-winter ice dam, this is a straightforward call — do the estimate comparison the one unhappy customer suggests, and ask exactly what's in the shingle package you're being quoted.
We recently had a roof replaced and after reaching out to several companies for estimates, we chose Woodland Homeworks.
A Stone Mason I trust recommended him and from the beginning he stood out. Tim was responsive, professional, and provided a detailed proposal within 24 hours.
While all three estimates we received were competitive, we ultimately chose Woodland because Tim took the time to answer all of our questions, followed up promptly and gave us confidence that the job will be done right.
Everything went exactly as promised. The crew arrived on schedule worked hard throughout the project, treated our property with respect and did an excellent job.
Our new roof looks fantastic and the entire experience went smoothly. I highly recommend Woodland Homeworks for anyone looking for a professional reliable roofing company.
We highly recommend Woodland Homeworks
Tim and his team came as a recommendation and did not disappoint. They did an amazing job from beginning to end. Thank you Tim & Team
Very happy with the overall experience and work. Job was explained and scouted. Measurements taken. Final bill was exactly what was quoted. I would recommend the team for another job.