Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 278+ reviews

Chilmark Roofing Experts. GAF Certified

Licensed, bonded, insured roofing contractor. Architectural shingle and metal roof specialists serving Chilmark. Same-day estimates. Manufacturer warranties up to 50 years.

12+
Years
500+
Projects
4.9
Rating
12+
Years Experience
500+
Projects Completed
4.9
Star Rating (278+ Reviews)
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Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Chilmark 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

A roof replacement in Chilmark typically runs $8,500 to $24,000 depending on the size and pitch. We give you an exact number upfront with a written proposal. No surprises on install day.

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 Chilmark crew can usually get there within 48 hours for non-emergency repairs.

storm damage repair
LICENSED

Storm Damage Repair

Storm damage claims in Massachusetts have a 1-year filing window with most carriers. Don't wait. We'll inspect your roof, document the damage, and help you file before the deadline. If there's no damage, we'll tell you that too.

new roof installation
TOP RATED

New Roof Installation

New roof installation on new construction means getting the ventilation right from the start. We calculate intake and exhaust requirements based on attic square footage and install the right combination of soffit vents and ridge vent. Saves you money on cooling bills in Massachusetts.

metal roofing
GUARANTEED

Metal Roofing

Standing seam metal roofing with Kynar 500/Hylar 5000 PVDF finish. The coating that keeps color for 40+ years without fading or chalking. We install Sheffield Metals and McElroy Metal panels in 24-gauge Galvalume steel with concealed Z-clips. UL 2218 Class 4 impact resistance. UL 790 Class A fire rating. Wind uplift tested to ASTM E1592. The only roof you'll ever need in Chilmark.

shingle roofing
INSURED

Shingle Roofing

Architectural shingles are what 80% of Chilmark homeowners choose. They look better than 3-tab, last longer, and handle wind better. We install GAF Timberline, Owens Corning Duration, and CertainTeed Landmark.

flat roofing
FREE ESTIMATE

Flat Roofing

TPO single-ply membrane in 60-mil or 80-mil thickness, hot-air welded seams, fully adhered or mechanically attached over polyiso insulation board. We install per NRCA and manufacturer specifications. Ponding water is the number one cause of flat roof failure. We use tapered ISO insulation to create minimum 1/4" per foot slope to drains. FM 4473 rated systems available for hail-prone Chilmark areas.

commercial roofing
SAME-DAY

Commercial Roofing

TPO is our most-requested commercial membrane in Massachusetts. Reflective, energy-efficient, and it welds together at the seams for a watertight bond. We install 60-mil and 80-mil systems with 15-20 year manufacturer warranties.

gutter installation
LICENSED

Gutter Installation

Improperly sized gutters cause fascia board rot and foundation erosion. We calculate gutter capacity using the rainfall intensity formula: roof square footage x pitch factor x rainfall rate (inches/hr for Chilmark). Standard 5" K-style handles 5,520 sq ft of effective roof area. Bigger roofs or steeper pitches need 6" gutters with 3x4" downspouts. We hang with hidden hangers screwed into rafter tails every 24".

roof inspection
TOP RATED

Roof Inspection

Our Chilmark roof inspections cover shingles, flashing, pipe boots, ridge vent, soffit, gutters, and decking condition. You get a written report with photos. If nothing's wrong, we tell you that.

emergency roof repair
GUARANTEED

Emergency Roof Repair

After we tarp and secure your roof, we document everything for insurance purposes. Photos, measurements, damage descriptions. Your adjuster gets a professional report, not a handwritten note.

skylight installation
INSURED

Skylight Installation

Skylight installation costs $1,200-$3,500 in Chilmark depending on size, type, and roof pitch. That includes the unit, flashing kit, interior trim, and roof patch-in. We handle everything from the outside in.

Why Choose Chilmark Roofing & Maintenance?

Trusted by homeowners and businesses across Chilmark.

4.9-Star Google Rating

278+ homeowners reviewed us. We don't pay for reviews or offer discounts for them. Those are real people who hired us and took the time to say we did a good job.

Manufacturer Certified

GAF Master Elite, Owens Corning Preferred, CertainTeed SELECT ShingleMaster. We carry certifications from the big three. That means factory-trained crews and the best available warranties.

Written Warranty

Manufacturer warranty plus our workmanship warranty in writing. If something fails because of our installation, we come back and fix it at no charge. Period.

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.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

Free Roof Inspection

Call (877) 586-1316 and we'll schedule an inspection at your convenience. Our Chilmark inspector checks every detail. Shingles, flashing, vents, gutters, decking condition.

2

Written Estimate

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

Expert Installation

Crew shows up on time with all materials pre-staged. Tarps go down, old roof comes off, new roof goes on. Most Chilmark homes are done in a single day.

4

Final Walkthrough

You see the finished roof, approve the work, and we register your manufacturer warranty on the spot. Written workmanship warranty handed to you at the walkthrough.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 278+ reviews
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"We had hail damage from the March storm. They met with our adjuster, got the roof approved for full replacement, and finished the job in one day. Five stars doesn't feel like enough."

L
Lisa H.
Chilmark
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"Used Chilmark Roofing & Maintenance for a leak repair over our bathroom. Turned out to be a cracked pipe boot โ€” $425 fix. Honest guys, could have told me I needed a new roof but they didn't."

R
Rachel G.
Chilmark
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"Asked for a second opinion because another company said I needed a full replacement. Chilmark Roofing & Maintenance said I only needed valley flashing repair and some shingle replacement. Saved me about $14,000. I trust these guys."

A
Amber G.
Chilmark

Service Areas

Areas We Serve

Chilmark Roofing & Maintenance serves Chilmark and the surrounding communities. If you're within 30 miles, we'll come to you.

Sterling West Bridgewater Abington Boylston Dennis Franklin Hyannis Melrose North Dighton Richmond
T

Meet the Owner

Tyler Miller

Owner & Lead Contractor

Tyler has been serving Chilmark for over 12 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 278+ five-star reviews."

License #996568 12+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Yes. We handle insurance claims regularly. It's a big part of what we do in Chilmark. Free inspection, photo documentation, claim filing assistance, and we meet the adjuster on-site. If the claim is approved, we do the work at the insurance-approved price. You pay your deductible and we handle the rest.

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 Chilmark and tarp the area to stop further damage.

Most residential roof replacements in Chilmark cost between $8,500 and $24,000. The price depends on your roof size (measured in squares, where 1 square = 100 sq ft), pitch, accessibility, and material choice. Architectural shingles are $350-$550 per square installed. We give free estimates with exact pricing.

We recommend GAF, Owens Corning, or CertainTeed. And we're certified by all three, so the choice is yours. In Chilmark, the most popular pick is GAF Timberline HDZ in Weathered Wood or Charcoal. For hail-prone areas, look at the impact-resistant versions rated UL 2218 Class 4. We walk you through the options during the estimate.

Poor ventilation causes premature aging. If your attic runs hot in summer and your shingles are curling at 15 years, bad ventilation is probably why. Missing shingles cause water intrusion and accelerate everything. We do a free inspection and give you a straight answer: repair, plan for replacement in 2-3 years, or replace now.

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 278+ Reviews  ยท  Licensed  ยท  Insured