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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.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
Woodland HomeWorks is a Billerica roofing and exterior crew that homeowners keep finding through word of mouth — review after review opens with some version of "recommended by a neighbor" or "came from a friend." Tim runs it, with his wife Aja handling the office and project managers Nick and Joe running the crews on-site, and the company's Massachusetts home improvement contractor registration is active. Roof replacement is the core of the work, and the specifics repeat: a full re-roof finished in one to two days, crews arriving early and working straight through, cleanup thorough enough that one reviewer said "you cannot even tell where the replaced shingle is." Siding, gutters, and skylights come up almost as often — several homeowners describe stripping decades-old aluminum or wood siding for vinyl, and in winter the crew turns up for ice dam removal and roof snow clearing, sometimes with next-day scheduling. In a 2024 review, one homeowner described finding old Gibson board sheathing and water damage mid-project; rather than paper over it, the crew flagged it and worked through the fix together. Across 128 reviews collected since 2022 — 12 of them in the last six months, none negative — the tone barely wavers: on-time crews, estimates that matched the final bill, and a project manager who checks in daily. The one sour note is a single review accusing the company of pricing nearly double other roofing contractors in the area and describing a high-pressure sales pitch — worth asking about directly when getting a quote, since it runs against how most other customers describe the sales process, a same-day or next-day proposal with no pressure to sign. Its Better Business Bureau page is an A+, accredited since July 2023, and lists roofing, siding, gutters and skylight installs among its certified services. Woodland HomeWorks is the call for a re-roof or a full exterior refresh — siding, gutters, and skylights along with it — especially when speed and daily cleanup matter. Get a written, itemized estimate and, given the one pricing complaint, a second quote to compare before signing.
Start to finish, top notch!
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.
Quality work with no surprises. Replaced the roof on our colonial in 2 days. Great team, easy to work with, amazing site cleanup!
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Certified attributes are verified against the public registry. Others are the business's own statement.
1 change recorded — last scanned Aug 3, 2026.
No stray nails in the yard three years later4.9