Local business · Middleton, MALocal business · 94 Newcombs Mill Rd, Middleton, MA 01949
Verified record
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Robert John Winters. 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
Sixty permits, and almost all of them are roofs. The permit trail behind this Middleton contractor reads like one trade practised over and over: strip the old roof, install GAF Timberline architectural shingles, or lay 060 EPDM rubber on a flat one — in Danvers, Tewksbury, Billerica, Everett, Brookline, Waltham, Newton Center and a string of Boston addresses. The work is documented rather than described. Nobody has written a review of it anywhere this scan could find: BuildZoom's profile, the only source with anything on this business, carries none. What it does carry is a filing history running from 2008 to December 2021, ranging from a $2,375 shingle-over in Everett to an $88,600 rubber-roof replacement on a Gainsborough Street multi-family in Boston. Two brick-repointing jobs and a siding permit sit alongside the roofing. On credentials, BuildZoom lists Massachusetts licence #CSSL-100902 — a Construction Supervisor Specialty licence carrying Roofing and Windows-and-Siding endorsements — and says it confirmed the licence active as of July 2026. Treat that as the directory's account rather than a check against the state. Separately, BuildZoom lists Home Improvement Contractor registration #109108 as inactive, and reports the Office of Consumer Affairs showed it cancelled at some point. That one matters: HIC registration is what backs a homeowner's access to the state Guaranty Fund, and a contractor doing siding and masonry alongside roofing is not covered by the roofing-only exemption. One more thing to pin down. The profile is titled Robert John Winters, but its own ownership block names Robert Winter, Robert A Winter and Robert Andrew Winter — a middle name and a surname that shift between the heading and the record. For a straightforward re-roof, the filing history is genuine evidence that this is someone who has done the work many times. Before signing, confirm both numbers directly with the Department of Public Safety and the Office of Consumer Affairs, get the exact registered name in writing, and ask what has been built since 2021 — the paper trail stops there.
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No changes recorded yet — last scanned Aug 17, 2026.
Fast storm response4.5
Free callbacks years after the warranty ends4.5
Fast turnaround4.5
Same-day roof jobs4.4