Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 158+ reviews

Cheswold, DE Roofing Contractor. Free Estimates

22+ years installing asphalt shingle roofs, metal roofing, and flat roof systems across Cheswold and Delaware. On the roof fast. Done right the first time.

22+
Years
500+
Projects
5
Rating
22+
Years Experience
500+
Projects Completed
5
Star Rating (158+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Cheswold 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

Full tear-off down to the decking, inspect every board, replace what's rotten, and install a complete roofing system from ice and water shield up. Most residential jobs finished in 1-2 days.

roof repair
SAME-DAY

Roof Repair

Step flashing at chimney walls is the number one leak source we see in Cheswold. Improper step flashing causes roof leaks. It's that simple. We install new step flashing with a chimney cricket for proper water diversion, sealed with Geocel tripolymer sealant. Fix it once, fix it right.

storm damage repair
LICENSED

Storm Damage Repair

Wind speeds over 60 mph cause shingle tab lift and seal failure. Hail over 1" diameter causes fractures through the shingle mat to the fiberglass reinforcement. Our HAAG-trained inspectors know the difference between cosmetic damage and functional damage. That distinction determines your insurance payout.

new roof installation
TOP RATED

New Roof Installation

Building a new home in Cheswold? Our crew works directly with your GC or we self-perform. We handle everything from the decking up: underlayment, ventilation design, material installation, and final inspection.

metal roofing
GUARANTEED

Metal Roofing

We do metal roof repairs too. Loose panels, failed sealant at transitions, rust spots on older galvanized. Not every metal issue needs a full replacement. Our Cheswold crew can usually fix it same-day.

shingle roofing
INSURED

Shingle Roofing

Asphalt shingle roofing is the most common and cost-effective roofing system in Cheswold. Our crews install 15-20 shingle roofs a month. We know the product inside and out. Nailing patterns, exposure measurements, hip and ridge details.

flat roofing
FREE ESTIMATE

Flat Roofing

Commercial flat roof replacement in Cheswold starts with a core sample to check the existing insulation. If it's waterlogged, everything comes off. If it's dry, we can sometimes overlay. Saves you $2-$4 per square foot.

commercial roofing
SAME-DAY

Commercial Roofing

Commercial roofing in Cheswold 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

Gutter replacement in Cheswold 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

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 replacement is often better than repair on units over 15 years old. VELUX FCM curb-mount replacement skylights install on the existing curb frame. No structural modification needed. Low-E laminated glass with argon fill for energy efficiency. Solar-powered blinds available for light control. VELUX No Leak guarantee when installed with the complete flashing system. Your Cheswold home gets more light, better insulation, and a proper warranty.

Why Choose Cheswold Roofing & Maintenance?

Trusted by homeowners and businesses across Cheswold.

5-Star Google Rating

158+ 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.

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.

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.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

Roof Evaluation

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

Crew shows up on time with all materials pre-staged. Tarps go down, old roof comes off, new roof goes on. Most Cheswold 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˜… 5/5 from 158+ reviews
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"Cheswold Roofing & Maintenance did our roof 4 years ago and I just had them do my mom's house too. Same quality, same crew lead actually. That tells you something about the company."

D
Dan M.
Cheswold
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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."

R
Ryan G.
Cheswold
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"Our insurance company tried to lowball us on the storm claim. Cheswold Roofing & Maintenance supplemented the estimate and got it approved for $7,000 more. They know the Xactimate system better than the adjuster did."

T
Tiffany W.
Cheswold

Service Areas

Areas We Serve

Cheswold Roofing & Maintenance provides roofing services throughout Cheswold and the greater DE area. Free estimates everywhere we serve.

Middletown Rehoboth Beach Yorklyn Delmar Harrington Milford Rockland Bear Dover Afb Hartly
T

Meet the Owner

Timothy Evans

Owner & Lead Contractor

Timothy has been serving Cheswold 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 158+ five-star reviews."

License #890836 22+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

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.

A typical Cheswold home with a 25-35 square roof runs $10,000-$18,000 for a full tear-off and install with architectural shingles. Steep-pitch homes and multi-story homes cost more because of safety requirements and access difficulty. Metal roofing is $12-$22 per sq ft. We quote exact numbers, not ranges.

We recommend GAF, Owens Corning, or CertainTeed. And we're certified by all three, so the choice is yours. In Cheswold, 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.

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.

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.

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 158+ Reviews  ยท  Licensed  ยท  Insured