Our Roofing Services | Chester, MA
Chester Roofing & Maintenance offers a complete range of roofing services in Chester and Orange, Saugus, Sudbury, West Hyannisport, Amesbury. Every job gets the same attention. Big or small.
Roof Replacement
We replace roofs. It's what we do more than anything else. Our Chester crews average 15-20 complete tear-off and replacements per month. That kind of volume means we've seen every situation: steep pitches, multiple layers, rotted decking, improper ventilation from the last guy. We fix all of it and install a roof system that's warranted for decades.
Get a Free Quote →Roof Repair
We warranty every repair for 5 years. If the same area leaks again due to our workmanship, we come back free. That warranty is in writing and it means something because we're a local Chester company. We're not disappearing.
Get a Free Quote →Storm Damage Repair
Wind damage and hail damage look different and require different documentation. Our HAAG-trained inspectors know what adjusters look for: granule displacement patterns, fractures in the shingle mat, seal failures, cracked ridge caps. Proper documentation is why our claims get approved.
Get a Free Quote →New Roof Installation
For Chester new builds, we recommend Tamko Heritage or Malarkey Vista AR for budget-conscious projects and Atlas Pinnacle Pristine with Scotchgard for algae-resistant performance. High-end builds get GAF Timberline HDZ or Owens Corning Duration STORM. Each carries different warranty tiers. We walk you through the comparison so you're choosing with real information, not marketing brochures.
Get a Free Quote →Metal Roofing
Standing seam metal is the longest-lasting residential roofing material you can install. 40-60 year lifespan, virtually zero maintenance, and it sheds hail and debris better than any shingle. Our Chester metal crews install residential and commercial standing seam, corrugated, and metal shingle profiles.
Get a Free Quote →Shingle Roofing
Shingle color matters more than you think. Dark shingles absorb heat. Great for cold Massachusetts winters, harder on cooling bills in summer. Lighter colors reflect heat. Algae-resistant granules prevent black streaking. We bring shingle samples to your Chester home so you can see them against your siding and trim.
Get a Free Quote →Flat Roofing
Modified bitumen is the best choice for residential flat roofs and low-traffic commercial applications in Chester. We torch-apply SBS-modified base and cap sheets in a two-ply system. Granulated cap sheet handles foot traffic and UV exposure. 15-20 year warranty.
Get a Free Quote →Commercial Roofing
Commercial roofing in Chester means flat and low-slope systems: TPO, EPDM, PVC, modified bitumen, and built-up roofing. We install and repair all of them. Retail, warehouse, office, restaurant, multi-family. Our commercial crew handles buildings from 2,000 to 100,000 square feet.
Get a Free Quote →Gutter Installation
We custom-form seamless aluminum gutters on-site from a continuous coil of .027 gauge stock. No factory seams means no seam failures. We form them to the exact length your fascia requires. One piece, one gutter, no leaks.
Get a Free Quote →Roof Inspection
Our 27-point residential roof inspection: (1) shingle condition and granule loss, (2) nail pops, (3) lifting tabs, (4) ridge cap integrity, (5) valley flashing, (6) step flashing at walls, (7) chimney flashing and counter-flashing, (8) drip edge condition, (9) pipe boot seals, (10) plumbing and HVAC vent integrity, (11) ridge vent function, (12) soffit ventilation, (13) gutter pitch and capacity, (14) downspout drainage, (15) fascia condition, (16) soffit condition, (17) ice dam evidence, (18) moss or algae growth, (19-27) attic: decking moisture, insulation displacement, rafter condition, bathroom exhaust routing, daylight penetration, ventilation balance, mold indicators, pest intrusion, previous repair evidence. Written report with annotated photos emailed same day.
Get a Free Quote →Emergency Roof Repair
Emergency protocol for active water intrusion: (1) interior containment. Buckets, plastic sheeting, water extraction if accessible, (2) exterior tarping with 20x30 heavy-duty poly sheeting over damaged area extending minimum 4 feet past damage on all sides, (3) secure with 2x4 nailer boards lag-screwed to the roof deck (not through shingles), (4) secondary tarp overlap for multi-section damage, (5) document with timestamped photos for insurance. Permanent repair scheduled within 48-72 hours once materials are sourced.
Get a Free Quote →Skylight Installation
Tubular skylights work where standard skylights can't. Interior bathrooms, hallways, closets. A reflective tube runs through the attic from a small rooftop dome to a ceiling diffuser. Brings in surprisingly good natural light. We install them in 2-3 hours.
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