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Residential and commercial roofing across Chelmsford, from postwar capes and split-levels to the flat-roof buildings along the town's commercial corridors.

Chelmsford grew fast in the postwar decades, and the housing shows it: capes, colonials, ranches, and split-levels, most of them now decades past their original roof. Add the commercial buildings along the town's busy corridors and you get a place that needs both steep-slope shingle work and flat membrane systems. Winter Hill does both.
For homeowners, the decision usually comes down to repair versus replace. Our free, photo-documented inspection settles it with evidence. If a repair will genuinely hold, we say so and do the repair. If the roof is done, we show you why, in photos, and price a complete GAF system: full tear-off, ice and water shield, synthetic underlayment, architectural shingles, and balanced ventilation.
For commercial owners and property managers, we install and repair TPO, EPDM rubber, roll roofing, and low-slope systems. As a GenFlex certified installer, we put membranes down to manufacturer spec and plan the work to keep your operation running.
The process never changes. Written, itemized proposals within a day or two. Permits pulled for you. Daily updates while the crew works. An on-schedule finish and a spotless site, with the dumpster removed promptly. Winter Hill has been family-owned since 2014, is GAF Master Elite certified, and is licensed and insured under HIC #204047. Hearth financing is available for residential projects.
Call (978) 704-3039 for a free roof inspection anywhere in Chelmsford. One visit, a full set of photos, and an honest written answer. Every proposal is itemized line by line, so you know what each dollar covers.
WHERE WE WORK
Andover, North Andover, Boxford, Lynnfield, Topsfield, Middleton, South Hamilton, Concord, Chelmsford, Burlington, Reading, Wakefield, Winchester, Lexington, and the surrounding towns. Free inspections across the service area.