Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 399+ reviews

Chesapeake City, MD Roofing Contractor. Free Estimates

Full tear-off and replacement down to the roof deck. Ice and water shield, synthetic underlayment, new flashing. No shortcuts. Serving Chesapeake City and Deale, Frostburg, Hollywood, Mardela Springs, Olney.

19+
Years
500+
Projects
5
Rating
19+
Years Experience
500+
Projects Completed
5
Star Rating (399+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Chesapeake City 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

Our Chesapeake City crews tear off and replace 15-20 roofs a month. That kind of volume means tight installs, clean job sites, and no wasted time. Most homes are done in a day. Two-story steep-pitch jobs take two.

roof repair
SAME-DAY

Roof Repair

Missing shingles cause water intrusion through the exposed underlayment and decking. We don't just replace the missing shingle. We check the deck for moisture damage with a Protimeter pin meter, replace any compromised underlayment, and weave new CertainTeed Landmark shingles into the existing pattern.

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 or an addition? We install new roofing systems from scratch. Decking inspection, ice and water shield, synthetic underlayment, ventilation calculations, and whatever material you want on top. Shingles, metal, or flat.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing in Maryland 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

Three-tab shingles are cheaper upfront but they don't hold up like architectural. We recommend them for sheds, detached garages, and rental properties where budget matters more than aesthetics. For your Chesapeake City home? Go architectural.

flat roofing
FREE ESTIMATE

Flat Roofing

We repair and install flat roofs on Chesapeake City 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

Your commercial roof is protecting your inventory, your equipment, and your employees. We do annual inspections for Chesapeake City business owners. Catch small problems before they become $50,000 problems.

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

Roof inspections after a storm are free. Always. We document hail hits, wind damage, and any pre-existing issues so your insurance claim is accurate and complete.

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

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

Why Choose Chesapeake City Roofing & Maintenance?

Trusted by homeowners and businesses across Chesapeake City.

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.

Licensed & Insured

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

5-Star Google Rating

399+ 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.

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

We Inspect First

Before we quote anything, we inspect everything. Shingles, flashing, pipe boots, ridge vent, soffit, gutters. You get a full written report with photos.

2

Written Estimate

We price by the roofing square with all materials itemized. You'll see exactly what you're getting. Shingle brand, underlayment type, ventilation specs, flashing details.

3

Expert Installation

Dumpster arrives at 7 AM. Tarps on the landscaping. Tear-off starts immediately. New ice and water shield, underlayment, drip edge, shingles, ridge vent. All in sequence.

4

Quality Check

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˜… 5/5 from 399+ reviews
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"Went with the Owens Corning Duration shingles in Estate Gray. The SureNail strip is legit. You can see each shingle is locked down tight. Happy with the choice."

M
Maria E.
Chesapeake City
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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."

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

A
Amber I.
Chesapeake City

Service Areas

Areas We Serve

Roofing Chesapeake City and Deale, Frostburg, Hollywood, Mardela Springs, Olney for 19+ years. Every roof we install gets the same attention whether it's across town or across the county.

Deale Frostburg Hollywood Mardela Springs Olney Rising Sun Sudlersville Whiteford Betterton
T

Meet the Owner

Todd Adams

Owner & Lead Contractor

Todd has been serving Chesapeake City 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 399+ five-star reviews."

License #643487 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Most residential roof replacements in Chesapeake City 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.

Manufacturer warranties range from 30 years to lifetime depending on the shingle line. Our workmanship warranty covers our labor and installation for the term stated in your contract. The best combo is the GAF Golden Pledge: 50-year material plus 25-year workmanship. That's what being a Master Elite contractor gets you.

Call (877) 586-1316 immediately. While you wait, put containers under any drips and move furniture and electronics away from the affected area. Take photos of the damage for insurance. Our Chesapeake City crew will tarp the leak source and schedule a permanent repair. Most emergency calls get same-day or next-day response.

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.

Yes. One day is standard for most residential jobs. We start early, work efficiently, and finish before dark. If your roof is larger than 40 squares or has a complex layout, it might push to day two. Either way, we seal everything watertight before we leave each night.

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˜… 5/5 from 399+ Reviews  ยท  Licensed  ยท  Insured