Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.8/5 from 366+ reviews

Professional New Canaan Roofing Contractor. Free Estimates

We've replaced 366+ roofs across Connecticut. GAF Timberline HDZ, Owens Corning Duration, CertainTeed Landmark. Licensed, insured, manufacturer-certified.

17+
Years
500+
Projects
4.8
Rating
17+
Years Experience
500+
Projects Completed
4.8
Star Rating (366+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in New Canaan 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

Replacing your roof isn't just about shingles. We install ice and water shield in the valleys and along eaves, synthetic underlayment across the whole deck, new drip edge on rake and eave, starter strip, and ridge vent. That's how a roof lasts 30 years in Connecticut.

roof repair
SAME-DAY

Roof Repair

Not every problem needs a full replacement. Sometimes it's a blown-off shingle, a cracked pipe boot, or deteriorated valley flashing. We diagnose the actual issue and fix that. We don't upsell you into a new roof you don't need.

storm damage repair
LICENSED

Storm Damage Repair

We work with every major insurance carrier. State Farm, Allstate, USAA, Liberty Mutual, Farmers, Nationwide. Our supplement team knows Xactimate line items and fights for full replacement when your roof qualifies.

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 Connecticut.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing costs more upfront at $12-$22 per sq ft installed in New Canaan 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

Commercial flat roof replacement in New Canaan 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

TPO is our most-requested commercial membrane in Connecticut. Reflective, energy-efficient, and it welds together at the seams for a watertight bond. We install 60-mil and 80-mil systems with 15-20 year manufacturer warranties.

gutter installation
LICENSED

Gutter Installation

Clogged gutters cause fascia rot. We see it on every other house in New Canaan. We install new gutters with proper pitch, adequate downspout capacity, and optional gutter guards if you're done cleaning them twice a year.

roof inspection
TOP RATED

Roof Inspection

Buying a home in New Canaan? Get an independent roof inspection before you close. Home inspectors look at the roof from the ground with binoculars. We get on it. Big difference.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Emergency roof repairs for active water intrusion follow a strict protocol: tarping with reinforced polyethylene sheeting secured to the roof deck, interior water extraction guidance, and temporary flashing at penetrations. Our New Canaan emergency crews carry 20x30 tarps, 2x4 nailer boards, and masonry anchors for various deck types. Permanent repairs are scheduled within 48-72 hours once materials are sourced.

skylight installation
INSURED

Skylight Installation

We install, replace, and repair skylights in New Canaan homes. Fogged glass, cracked frames, persistent leaks around old skylights. We fix it all. Sometimes replacing a 20-year-old skylight is cheaper than trying to repair it.

Why Choose New Canaan Roofing & Maintenance?

Trusted by homeowners and businesses across New Canaan.

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.

Licensed & Insured

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

17 Years in New Canaan

We've been roofing New Canaan homes since before half these companies had a website. 17 years means we know the local codes, the weather patterns, and the materials that hold up here.

4.8-Star Google Rating

366+ 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

roof replacement project
roof repair project
storm damage repair project
View All Projects โ†’

Simple Process

How It Works

1

Schedule Your Inspection

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

2

Written Estimate

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

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

Warranty Activation

We walk the property with you, show you the finished roof, answer any questions. Then we run the magnetic nail sweep and clean up every scrap of debris.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.8/5 from 366+ reviews
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"The crew showed up at 7:30 and was done by 4. Old roof off, new one on, yard cleaned up. I watched from the window. These guys don't mess around."

K
Karen G.
New Canaan
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"Had a flat roof leak on our commercial building downtown. New Canaan Roofing & Maintenance patched it temporarily, then came back and did a full TPO replacement the next week. Solved a problem we'd been chasing for two years."

A
Andrea C.
New Canaan
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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."

R
Ryan P.
New Canaan

Service Areas

Areas We Serve

Our service area includes New Canaan and all surrounding communities within Cheshire, East Haven, Harwinton, Moodus, Norwalk. We don't charge extra for travel.

Cheshire East Haven Harwinton Moodus Norwalk Riverton Stonington West Hartford Baltic Chester
J

Meet the Owner

Jason Wilson

Owner & Lead Contractor

Jason has been serving New Canaan for over 17 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 366+ five-star reviews."

License #710310 17+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

A typical New Canaan 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.

Most residential roofs in New Canaan 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.

There's no single "best" shingle. It depends on what you need. For warranty coverage, GAF Timberline HDZ with Golden Pledge is the best in the industry. For wind resistance, Owens Corning Duration with SureNail locks down tight. For value, CertainTeed Landmark or IKO Cambridge give you solid performance at a lower price point. We carry all of them.

Catch the water with a bucket, move valuables out of the drip zone, and call us at (877) 586-1316. Don't get on the roof yourself. It's dangerous and you probably can't fix it permanently anyway. We respond to emergency leaks within 24 hours in New Canaan and tarp the area to stop further damage.

We partner with GreenSky and Hearth for roofing financing. Options include 12-month same-as-cash (0% if paid in full within 12 months), 5-year fixed rate, and 7-10 year extended plans. Monthly payments on a $15,000 roof run about $150-$250/month depending on the term. Apply during the estimate.

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 366+ Reviews  ยท  Licensed  ยท  Insured