Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 405+ reviews

Cheshire Roofing Contractor. Licensed & Insured

23+ years installing asphalt shingle roofs, metal roofing, and flat roof systems across Cheshire and Connecticut. Free inspections. Financing available.

23+
Years
500+
Projects
4.9
Rating
23+
Years Experience
500+
Projects Completed
4.9
Star Rating (405+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Cheshire 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

Roof repairs get worse when you ignore them. A $400 flashing repair turns into $4,000 of water damage inside the wall. Our Cheshire crew can usually get there within 48 hours for non-emergency repairs.

storm damage repair
LICENSED

Storm Damage Repair

HAAG Certified Inspector on every storm claim we handle in Cheshire. HAAG certification is the insurance industry standard for forensic roof inspection. Adjusters trust our reports. We document hail hits per square, wind creasing, and granule displacement. FM 4473 hail resistance ratings determine whether your roof qualifies for full replacement or spot repair.

new roof installation
TOP RATED

New Roof Installation

We price new installs by the roofing square (100 sq ft). Architectural shingles in Cheshire typically run $350-$550 per square installed, depending on the pitch and access. That includes materials, labor, cleanup, and warranty registration.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing costs more upfront at $12-$22 per sq ft installed in Cheshire compared to $4-$8 for shingles. But it lasts 2-3x longer and your energy bills drop 15-25%. Math works out over time.

shingle roofing
INSURED

Shingle Roofing

Your shingle choice determines your warranty, your curb appeal, and how your roof handles Connecticut 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

A flat roof that's ponding water is a flat roof with a problem. We install tapered insulation systems to create positive drainage to your scuppers or interior drains. No more standing water after rain.

commercial roofing
SAME-DAY

Commercial Roofing

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

gutter installation
LICENSED

Gutter Installation

We install 5" and 6" seamless aluminum gutters in Cheshire. 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 27-point roof inspection covers: shingle condition, granule loss, nail pops, lifting tabs, ridge cap integrity, valley flashing, step flashing at walls, drip edge, pipe boot seals, vent function, soffit ventilation, gutter pitch, downspout capacity, fascia condition, decking (from attic if accessible), and visible signs of moisture in the attic. Written report with photos emailed same day.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Fallen tree limb damage requires structural assessment before repair. We check rafter integrity, decking condition, and whether the ceiling joists below were impacted. If structural members are cracked or displaced, you need a framing carpenter before we re-roof. We coordinate with trusted Cheshire contractors for structural work. Insurance carriers require separate line items for structural vs. roofing repairs. We document both.

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 Cheshire Roofing & Maintenance?

Trusted by homeowners and businesses across Cheshire.

4.9-Star Google Rating

405+ 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.

Free Roof Inspection

We get on the roof, take photos, and give you an honest assessment. If you don't need work, we'll tell you. No charge, no obligation, no high-pressure sales pitch.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

We Inspect First

We climb up, walk the entire roof, and document what we find with photos and measurements. Takes about 30 minutes. You'll see exactly what we see.

2

No-Surprise Quote

You get a written proposal with material specs, labor breakdown, timeline, and total cost. The number on the quote is the number you pay. No change orders, no hidden fees.

3

Build Day

Our crews average 8 years of experience each. They tear off the old roof, inspect the decking, replace any damaged boards, and install your new system from the deck up.

4

Final Walkthrough

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˜… 4.9/5 from 405+ reviews
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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."

T
Tiffany N.
Cheshire
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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."

T
Tony I.
Cheshire
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"Got three quotes for a roof replacement. Cheshire Roofing & Maintenance was the middle price but the only one who actually got on the roof and showed me photos. Everyone else just eyeballed it from the driveway."

M
Mark K.
Cheshire

Service Areas

Areas We Serve

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

Farmington Litchfield New Milford Pine Meadow Shelton Torrington Wilton Branford Cromwell Gales Ferry
S

Meet the Owner

Shane Campbell

Owner & Lead Contractor

Shane has been serving Cheshire for over 23 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 405+ five-star reviews."

License #748828 23+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

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

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 Connecticut.

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 Cheshire crew will tarp the leak source and schedule a permanent repair. Most emergency calls get same-day or next-day response.

Depends on size, pitch, and materials. Average in Cheshire 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.

You get two warranties: one from the manufacturer on the materials and one from us on the workmanship. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on the shingle. Owens Corning and CertainTeed have similar programs. Our own workmanship warranty is in writing and covers installation defects.

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 405+ Reviews  ยท  Licensed  ยท  Insured