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

Pittsville Roof Repair & Replacement | 20+ Years

Hail damage? Missing shingles? Call (877) 586-1316 today. Free roof inspection and insurance claim assistance in Pittsville. Free inspections. Financing available.

20+
Years
500+
Projects
4.8
Rating
20+
Years Experience
500+
Projects Completed
4.8
Star Rating (380+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Pittsville 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

Owens Corning Duration shingles with SureNail technology rated to ASTM D3462 and D7158 Class H wind resistance. Our Pittsville crews install TruDefinition Duration in a full Owens Corning system. ProArmor synthetic underlayment, VentSure ridge vent, and Starter+ starter strip. Preferred Protection warranty included.

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 Pittsville 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 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 Maryland.

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 Pittsville.

shingle roofing
INSURED

Shingle Roofing

Your shingle choice determines your warranty, your curb appeal, and how your roof handles Maryland weather. We'll show you samples, explain the differences, and let you pick what fits your budget. No pressure.

flat roofing
FREE ESTIMATE

Flat Roofing

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

commercial roofing
SAME-DAY

Commercial Roofing

Modified bitumen (mod-bit) is still the best choice for high-traffic commercial roofs in Pittsville. We torch-apply SBS-modified base and cap sheets over properly primed concrete or approved decking. Two-ply mod-bit systems carry 20-year NDL (No Dollar Limit) warranties through GAF, Firestone, or Johns Manville. NRCA member. We follow the manual.

gutter installation
LICENSED

Gutter Installation

If your gutters overflow during rain, they're either clogged, undersized, or pitched wrong. Sometimes all three. We'll assess the issue and fix it. Might be a cleaning, might be a replacement.

roof inspection
TOP RATED

Roof Inspection

Our Pittsville 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

Tree through the roof at 2 AM? Active leak flooding your kitchen? Call (877) 586-1316. We answer after hours for emergencies. Our Pittsville emergency crew can be on-site within hours.

skylight installation
INSURED

Skylight Installation

Skylights bring natural light into rooms that don't have it. Bathrooms, hallways, closets. We install VELUX and Fakro fixed and vented skylights with proper flashing kits designed for asphalt shingle roofs.

Why Choose Pittsville Roofing & Maintenance?

Trusted by homeowners and businesses across Pittsville.

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.

GAF Master Elite Contractor

Only 3% of roofers earn this certification. It means we can offer the Golden Pledge warranty: 25-year workmanship plus 50-year materials. Best warranty in roofing, full stop.

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.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

We Inspect First

Our inspector walks the roof looking at shingle condition, flashing integrity, vent function, and signs of moisture underneath. 30-45 minutes for most Pittsville homes.

2

Transparent Pricing

Multiple material options at different price points so you can compare. GAF, Owens Corning, CertainTeed. We install all three and let you pick what fits your budget.

3

Roof Goes On

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

Inspection & Cleanup

Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.8/5 from 380+ reviews
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"Asked for a second opinion because another company said I needed a full replacement. Pittsville Roofing & Maintenance said I only needed valley flashing repair and some shingle replacement. Saved me about $14,000. I trust these guys."

K
Kevin S.
Pittsville
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"Had them install a ridge vent to replace the old box vents. Attic runs about 15 degrees cooler now. Should've done it when we got the roof but better late than never."

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

S
Steve C.
Pittsville

Service Areas

Areas We Serve

Our roofing crews work across Pittsville, Fulton, Hunt Valley, Marriottsville, Owings Mills, Riverdale, and everywhere in between. Local company, local crews.

Fulton Hunt Valley Marriottsville Owings Mills Riverdale Sunderland Williamsport Bishopville Chestertown Dickerson
T

Meet the Owner

Troy Cooper

Owner & Lead Contractor

Troy has been serving Pittsville for over 20 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 #159094 20+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Absolutely. A new roof shouldn't mean emptying your bank account. We have 0% intro options, low fixed-rate plans, and extended terms up to 12 years. Quick credit check, fast approval, and you can get your roof done this month instead of waiting until you've saved enough.

The shingles carry the manufacturer's warranty. Typically 30-50 years for architectural shingles. Our installation warranty covers any defects in our workmanship. If something goes wrong because of how we installed it, we fix it at no cost. Both warranties are in writing and we provide them at the final walkthrough.

Most residential roof replacements in Pittsville 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.

Yes. We handle insurance claims regularly. It's a big part of what we do in Pittsville. 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.

Age is the biggest factor. If your shingles are 20+ years old and you're seeing curling, cracking, or granule buildup in the gutters, it's time. Other red flags: leaks, missing shingles, daylight in the attic, and your neighbors all getting new roofs (same-age homes in a subdivision often need replacement around the same time).

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