Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 170+ reviews

Jamaica Plain Area Roofing Experts. GAF Certified

GAF-certified roofing contractor installing architectural shingles, impact-resistant Class 4 materials, and standing seam metal roofs in Jamaica Plain. Serving Jamaica Plain and Stow, West Harwich, Agawam, Brighton, Dorchester Center.

19+
Years
500+
Projects
4.9
Rating
19+
Years Experience
500+
Projects Completed
4.9
Star Rating (170+ Reviews)
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Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Jamaica Plain โ€” from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.

roof replacement
FREE ESTIMATE

Roof Replacement

We don't do shortcuts on replacements. Tear off the old roof, check the decking for soft spots, install synthetic underlayment, drip edge, starter strip, shingles, ridge vent. The whole system. Your roof is only as good as the layers underneath.

roof repair
SAME-DAY

Roof Repair

Roof repairs get worse when you ignore them. A $400 flashing repair turns into $4,000 of water damage inside the wall. Our Jamaica Plain crew can usually get there within 48 hours for non-emergency repairs.

storm damage repair
LICENSED

Storm Damage Repair

Our storm damage process: free inspection, full photo documentation, direct filing with your insurance carrier, meet the adjuster on-site, and handle the repairs once approved. We don't ask for money upfront on insurance claims.

new roof installation
TOP RATED

New Roof Installation

New construction roof installation following IRC Section R905 and local Jamaica Plain building code amendments. We calculate ventilation per IRC R806 (1:150 ratio reduced to 1:300 when 50% is within 3ft of ridge. Synthetic underlayment per ASTM D226, ice barrier per ASTM D1970 at eaves in freeze-thaw climate zones. Manufacturer-certified installation locks in the full system warranty.

metal roofing
GUARANTEED

Metal Roofing

We install 24-gauge and 26-gauge standing seam in Galvalume and pre-painted steel. Concealed fastener system means nothing's exposed to weather. Panels lock together at the seam and clip to the roof deck.

shingle roofing
INSURED

Shingle Roofing

GAF Timberline HDZ architectural shingles with StrikeZone nailing area. The highest-selling shingle in North America. Impact-rated to UL 2218 Class 4 when installed with the full GAF Roof System. Our Jamaica Plain crews install Timberline in the full system configuration to qualify for Golden Pledge warranty. ASTM D3462 and D7158 Class H certified.

flat roofing
FREE ESTIMATE

Flat Roofing

Modified bitumen is our go-to for residential flat roofs in Jamaica Plain. Two-ply torch-applied system with a granulated cap sheet. It handles foot traffic, thermal cycling, and Massachusetts UV better than single-ply at the residential scale.

commercial roofing
SAME-DAY

Commercial Roofing

Roof coatings can extend the life of your commercial roof by 10-15 years for a fraction of replacement cost. We apply silicone and acrylic coatings over existing TPO, EPDM, and metal substrates. Not every roof qualifies. We'll be straight with you.

gutter installation
LICENSED

Gutter Installation

Gutter replacement in Jamaica Plain runs $8-$15 per linear foot installed, depending on material and story height. That includes hangers every 24 inches, end caps, miters, and outlet drops. We custom-form everything on-site.

roof inspection
TOP RATED

Roof Inspection

Annual roof inspections catch small problems before they become expensive ones. A cracked pipe boot is a $150 fix. Ignoring it means $3,000 in ceiling and wall water damage. We recommend an inspection every 2-3 years for roofs under 10 years old, and annually after that.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Emergency roof repairs for active water intrusion follow a strict protocol: tarping with reinforced polyethylene sheeting secured to the roof deck, interior water extraction guidance, and temporary flashing at penetrations. Our Jamaica Plain emergency crews carry 20x30 tarps, 2x4 nailer boards, and masonry anchors for various deck types. Permanent repairs are scheduled within 48-72 hours once materials are sourced.

skylight installation
INSURED

Skylight Installation

Vented skylights open to let hot air escape. Great for kitchens and bathrooms in Jamaica Plain. Fixed skylights are cheaper and simpler. Solar-powered options from VELUX qualify for the federal 30% tax credit through 2032.

Why Choose Jamaica Plain Roofing & Maintenance?

Trusted by homeowners and businesses across Jamaica Plain.

Free Roof Inspection

We get on the roof, take photos, and give you an honest assessment. If you don't need work, we'll tell you. No charge, no obligation, no high-pressure sales pitch.

Financing Available

A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.

Clean Job Sites

We run magnetic nail sweeps three times. Once during tear-off, once after install, once before we leave. Tarps on the ground, dump trailer in the driveway. Your yard looks the same when we're done.

Insurance Claims Handled

Storm damage? We work with your insurance company directly. Free inspection, Xactimate documentation, adjuster meeting on-site. We fight for full replacement when your roof qualifies.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

Roof Evaluation

Free 27-point inspection covering every component of your roofing system. Photos shared with you on the spot. No obligation to hire us. The information is yours.

2

Detailed Quote

We email or text the proposal so you can review it at home. Questions? Call us. No pressure, no expiration date tricks, no "today-only" pricing.

3

Professional Crew

No subcontractors. Our crews, our equipment, our supervision. A project manager checks in throughout the day and does a final quality inspection before cleanup.

4

Final Walkthrough

Our project manager does a final inspection against the manufacturer's installation checklist. We register your warranty the same day. You get the paperwork within a week.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 170+ reviews
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"Asked for a second opinion because another company said I needed a full replacement. Jamaica Plain Roofing & Maintenance said I only needed valley flashing repair and some shingle replacement. Saved me about $14,000. I trust these guys."

E
Eric O.
Jamaica Plain
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"I got a new metal roof. Standing seam in charcoal. Not cheap, but it looks like a completely different house. Their metal crew clearly knows what they're doing. Seams are dead straight."

P
Paul B.
Jamaica Plain
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"The crew showed up at 7:30 and was done by 4. Old roof off, new one on, yard cleaned up. I watched from the window. These guys don't mess around."

M
Matt V.
Jamaica Plain

Service Areas

Areas We Serve

From Jamaica Plain to Stow, West Harwich, Agawam, Brighton, Dorchester Center. We've replaced roofs on every street. Ask your neighbor. Chances are we did theirs.

Stow West Harwich Agawam Brighton Dorchester Center Gill Ipswich Middleboro North Hatfield Rockport
S

Meet the Owner

Shane Cooper

Owner & Lead Contractor

Shane has been serving Jamaica Plain for over 19 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company โ€” but the values haven't changed.

"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 170+ five-star reviews."

License #118378 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

You get two warranties: one from the manufacturer on the materials and one from us on the workmanship. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on the shingle. Owens Corning and CertainTeed have similar programs. Our own workmanship warranty is in writing and covers installation defects.

Catch the water with a bucket, move valuables out of the drip zone, and call us at (877) 586-1316. Don't get on the roof yourself. It's dangerous and you probably can't fix it permanently anyway. We respond to emergency leaks within 24 hours in Jamaica Plain and tarp the area to stop further damage.

We install GAF Timberline HDZ, Owens Corning Duration, and CertainTeed Landmark. The three most popular architectural shingles in the country. All three are solid choices. GAF gives us access to the Golden Pledge warranty (25-year workmanship). Owens Corning Duration has SureNail technology for wind resistance. CertainTeed Landmark is a reliable mid-range option. We help you choose based on budget, color preference, and warranty goals.

Here's the process: we inspect your roof for free, document any storm damage with photos, and help you file the claim. Your insurance company sends an adjuster. We meet them on-site and walk the roof together. If approved, we do the work at the agreed price. If the estimate seems low, we supplement it with additional documentation.

One day for most homes. Our crews are experienced and we pre-stage materials the day before install. Bigger or steeper roofs can run to two days. The dumpster shows up at 7 AM and leaves when we're done. Your life gets back to normal fast.

Have more questions? Call (877) 586-1316

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

📞 Call (877) 586-1316

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 170+ Reviews  ยท  Licensed  ยท  Insured