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 Winter Hill Builders. 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.
— repeatedly finished on schedule, one job inside a single day
Deck and porch rebuilds — full teardowns and composite replacements described by customers
Permits handled — Historic Commission approval and building permit obtained on a porch
Named project managers — customers credit daily updates from specific staff
Clean sites — daily waste disposal and thorough final cleanup noted often
Repeat hires — several customers on their second or third project
Contract disputes — a 2025 reviewer reports charges well above the contract
Final inspection skipped — the same reviewer says none was completed
Schedule creep — a two-week job ran three months with two price increases
Material substitutions — cabinets delivered were not the ones quoted
Billing friction — a customer describes the office nickel-and-diming extras
Thin recent record — little written since early 2026 despite a deep history
Winter Hill Builders is an envelope company first: roofs, porches, decks, siding. Out of Danvers, with a verified-active Massachusetts home improvement contractor registration and an A+ BBB accreditation, it carries 4.8 stars across 67 Google ratings, and the pattern in them is that customers name the person who ran their job — Robert on the contract, Ana on scheduling, Mateus, Gustavo, Alex and Cesar on the crews.
The jobs described are the awkward ones. A March 2026 customer had a wooden deck torn out and rebuilt in composite on the same footprint, with the carpenter reworking a gate underneath so it still functioned. In September 2025 a crew stripped and replaced a flat rubber roof over six straight days through a heat wave; another September 2025 customer had a chimney taken down, the roof sealed over it and the fireplace refaced — one job most companies would split in two. A February 2025 front porch had to come down entirely, and the company handled both the Historic Commission approval and the building permit. When a windstorm drove a large branch through a house in April 2025, they handled the repair.
Speed and cleanliness come up constantly. An August 2024 customer had a roof and rake boards finished in a single day including cleanup; several reviewers mention daily waste disposal and a site left cleaner than it was found. Repeat hires are common — one customer counts three projects, another two, another describes siding first and then a full detached-garage rebuild with new roof, siding, windows and structural repairs.
The complaints are about paperwork and scope, not craft. An October 2025 reviewer says the company did not abide by its contract, charged well above it, never completed a final inspection, and that a separate inspector found the transition between the roof and the lower levels incorrectly installed — with promised extra plywood never delivered; that reviewer also alleges the positive ratings come from people connected to the company. A December 2023 customer's two-week job ran three months with the price rising twice. A January 2024 bathroom remodel, praised for its quality, ran from late September to late November 2023 and came with an office manager the customer felt was nickel-and-diming them. An October 2023 customer got cabinets that were good quality but not the ones specified in the quote.
Worth knowing: the written record is concentrated in 2024 and 2025, with little added in the last six months, so the current pace is harder to read than the history. For a roof, a deck, a porch rebuild or a siding package this is a strong shortlist candidate. Before signing, get the material specifications written into the contract rather than the proposal, agree in writing how change orders and price increases get approved, and confirm who performs the final inspection and when.
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Most recent comments
5.0Mar 8, 2026
We had an excellent experience with Winter Hill Builders for tear out of a wooden deck and replacement with a composite deck in the same footprint. I especially appreciated Matt's consistent updates on progress, the carpenter's creative work making a gate underneath the deck work with the layout, and the quick timeline on which they got the entire job done. Highly recommended.
I recently had my roof completely replaced and couldn’t be happier with the experience, and price was reasonable. From the initial estimate to the final cleanup, the entire process was smooth, professional and efficient and clearly knew what they were doing. They explained everything upfront, answered my questions, and kept me informed.<br><br>The quality of the workmanship is excellent, and the new roof looks fantastic. I highly recommend them to anyone looking for a reliable, honest, and skilled roofing company. Thank you to Alex and Gregory for continuing to follow and getting back to me when I had questions.
We were lucky to find Winter Hill Builders! Their professionalism, efficiency, and integrity are exceptional, and the entire process was seamless. We wholeheartedly recommend them to anyone who wants quality work done quickly and stress-free.
Excellent professional service and work crews. Respectful of our property cleaned daily waste disposal and answered questions or got untouched with someone who could. Our wants and design needs met fully.<br>Brian and Caesar were available daily checking on the workers and making sure work got completed but also we were satisfied.<br>Outstanding customer service and care.
The team at Winter Hill are professionals and exceeded my expectations. Robert and team communicated options, timelines, and explained everything along the way for our roof replacement. The project started on time, finished on time, all while addressing the unexpected.<br><br>This is the company that you want to work on your HOME. I would gladly choose them for future projects.