Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.8/5 from 380+ reviews

Trusted Osterville Roofing Experts. Free Estimates

Owens Corning Preferred, GAF Master Elite, CertainTeed certified. Manufacturer warranties up to 50 years on your Osterville roof. Free inspections. Financing available.

22+
Years
500+
Projects
4.8
Rating
22+
Years Experience
500+
Projects Completed
4.8
Star Rating (380+ Reviews)
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Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Osterville 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 handle the whole replacement from permits to final inspection. Our Osterville office pulls the permit, coordinates the dumpster, runs the crew, and schedules the building inspector. You sign the contract and we handle the rest.

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

storm damage repair
LICENSED

Storm Damage Repair

Hail, wind, fallen branches. Massachusetts storms do real damage to roofs. We respond within 24 hours, tarp exposed areas to prevent further damage, and start your insurance claim with a detailed inspection report.

new roof installation
TOP RATED

New Roof Installation

We install new roofs on new construction, room additions, detached garages, and covered patios. Our Osterville crews handle residential and light commercial. Standard install time is 1-3 days depending on size.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing in Massachusetts makes sense. It reflects heat, handles high winds, and sheds hail better than shingles. We install standing seam, corrugated, and metal shingle panels.

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 Osterville 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

We repair and install flat roofs on Osterville homes, garages, commercial buildings, and additions. TPO for reflectivity, EPDM for budget, PVC for chemical resistance near restaurants and kitchens.

commercial roofing
SAME-DAY

Commercial Roofing

Commercial roofing in Osterville means dealing with rooftop HVAC units, drains, parapet walls, and penetrations. We work around your equipment and schedule repairs or installs to minimize business disruption.

gutter installation
LICENSED

Gutter Installation

We install 5" and 6" seamless aluminum gutters in Osterville. Standard homes get 5", high-volume areas and steeper pitches get 6". Downspouts every 30-40 ft of gutter run with splash blocks or underground drains.

roof inspection
TOP RATED

Roof Inspection

Our Osterville 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

Most emergency roof repairs in Osterville are storm-related. High winds rip off ridge caps and shingles. Fallen limbs puncture the decking. We respond fast, tarp the damage, and coordinate the permanent fix. Including insurance paperwork if applicable.

skylight installation
INSURED

Skylight Installation

A skylight installed wrong will leak. The flashing has to integrate with the shingle courses. Step flashing on the sides, headwall flashing on top, and a sill pan underneath. We use manufacturer flashing kits because they're engineered to work with the skylight frame.

Why Choose Osterville Roofing & Maintenance?

Trusted by homeowners and businesses across Osterville.

4.8-Star Google Rating

380+ 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.

Licensed & Insured

Fully licensed, bonded, and insured in Massachusetts. We carry $2M in general liability. Workers' comp on every crew member. Your property is protected if anything goes sideways.

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.

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

roof replacement project
roof repair project
storm damage repair project
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

Your Custom Proposal

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

Build Day

We build your roof the way manufacturers require for full warranty coverage. Every layer matters. Ice and water shield, synthetic underlayment, starter strip, field shingles, hip and ridge caps.

4

Inspection & Cleanup

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˜… 4.8/5 from 380+ reviews
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"They replaced our gutters along with the roof. Seamless aluminum, everything matches. No more overflow when it rains hard. Wish I'd done this years ago."

A
Ashley T.
Osterville
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"Had a huge oak branch go through the roof during a storm. Osterville Roofing & Maintenance tarped it the same night and had the repair done two days later. Insurance covered everything and they handled the whole claim."

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

R
Robert P.
Osterville

Service Areas

Areas We Serve

Our roofing crews work across Osterville, Carlisle, East Brookfield, Hadley, Leicester, Monroe Bridge, and everywhere in between. Local company, local crews.

Carlisle East Brookfield Hadley Leicester Monroe Bridge Norwood Salem Stoneham West Chesterfield Acushnet
R

Meet the Owner

Rebecca Johnson

Owner & Lead Contractor

Rebecca has been serving Osterville for over 22 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 380+ five-star reviews."

License #590766 22+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Absolutely. Our team includes HAAG Certified Inspectors who document storm damage the way insurance adjusters expect. We file the claim, meet the adjuster, handle supplements if the initial estimate is low, and complete the repairs. We work with every major carrier in Massachusetts.

Depends on size, pitch, and materials. Average in Osterville is $12,000-$16,000 for a standard residential replacement with architectural shingles. We price by the square and itemize everything so you can compare to other quotes. Free estimates. Call (877) 586-1316.

Most residential roofs in Osterville are done in one day. We show up at 7 AM, tear off the old roof, install the new system, and clean up by end of day. Two-story homes, steep pitches, or large roofs might take two days. We never leave a house uncovered overnight.

First: put a bucket or container under the drip. If there's a visible bulge in the ceiling, carefully poke a small hole to let water drain into a bucket. This prevents the ceiling from collapsing. Then call (877) 586-1316. We do emergency tarping and temporary leak stops within 24 hours. The permanent repair follows once conditions allow.

Yes. We offer 12-month same-as-cash, low-interest plans up to 144 months, and no-money-down options through GreenSky and Hearth. Credit approval takes about 5 minutes. A new roof is a major expense. Financing lets you get it done now without draining your savings.

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˜… 4.8/5 from 380+ Reviews  ยท  Licensed  ยท  Insured