Before You Hire a Roofer in NY or CT: The Complete Checklist

Here's what a lot of homeowners don't realize: New York State does not have a statewide roofing license. There's no state board that certifies roofers the way there is for plumbers or electricians. What that means is that licensing requirements vary by county and town.

In Westchester County, home improvement contractors (including roofers) must register with the county Department of Consumer Protection. The registration number starts with "WC-" and should appear on every contract and advertisement. You can verify a contractor's registration at consumer.westchestergov.com or by calling (914) 995-2155.

In Connecticut, roofers must hold a Home Improvement Contractor (HIC) registration from the Department of Consumer Protection. The number format is "HIC.XXXXXX" and you can verify it at elicense.ct.gov. This is a real registration with the state — not just a business license.

Rockland, Putnam, Dutchess, and Orange counties in NY have their own local requirements. Always ask your town building department whether the contractor needs a local registration.

Bottom line: If a roofer can't give you a license or registration number, move on. It's the absolute minimum bar.

Every roofing contractor should carry two types of insurance, and you should verify both before any work starts:

General Liability Insurance — covers damage to your property during the job. If a worker drops a tool through your skylight or damages your siding removing old shingles, this pays for the repair. Minimum coverage should be $1 million per occurrence. Many reputable roofers carry $2 million.

Workers' Compensation Insurance — covers injuries to workers on your property. This is the one people forget. If a roofer falls off your roof and doesn't have workers' comp, YOU can be held liable for their medical bills under New York and Connecticut law. This isn't hypothetical — it happens.

How to verify: Ask the contractor for a Certificate of Insurance (COI). Then call the insurance company listed on the certificate and confirm the policy is active. Contractors whose insurance has lapsed will still show you the old certificate. A 5-minute phone call protects you from a potential lawsuit.

A professional roofing quote should be detailed enough that you can compare it apples-to-apples with another contractor's quote. If someone hands you a one-line quote that just says "roof replacement — $12,000," that's not enough information to evaluate.

A proper quote should specify:

Materials: What brand and product line of shingles (e.g., "GAF Timberline HDZ" or "CertainTeed Landmark"). What underlayment (synthetic vs felt). What flashing material (aluminum vs copper). The specific brand matters because quality varies enormously — a "30-year shingle" from one manufacturer isn't the same as another's.

Scope of work: Full tear-off or overlay (tear-off is almost always better). Number of layers being removed. Whether they're replacing the drip edge, ice and water shield in the valleys, and pipe boot flashings. Whether chimney flashing is included or extra.

Warranty: There are two warranties — the manufacturer's material warranty (typically 25-50 years) and the contractor's workmanship warranty (typically 5-10 years). Both matter. A manufacturer's warranty only covers defective shingles, not installation errors. The workmanship warranty is where the contractor stands behind their work.

Permit and dumpster: Are these included in the price? Some contractors quote low and then add $300-600 for permits and dumpster on top.

Payment terms: Never pay more than 30% upfront. Standard is 10-30% deposit, remainder on completion. Any contractor asking for 50%+ upfront is a red flag.

These aren't minor concerns — any one of them is reason to find a different contractor:

1. They showed up at your door after a storm. Legitimate roofers don't need to knock on doors. Storm chasers travel from disaster to disaster, do fast low-quality work, and are gone before the problems show up. They're often from out of state and impossible to reach for warranty claims.

2. They can't provide a written contract. New York and Connecticut both require written contracts for home improvement work over $500 (NY) or any amount (CT). A contractor who wants to work on a handshake is either ignorant of the law or deliberately avoiding accountability. Either way, not someone you want on your roof.

3. They want to "work with your insurance company" on the price. This is a common scam where the contractor inflates the insurance claim, keeps the excess, and does the minimum work. It's insurance fraud, and you're the one who signed the claim form. If your roof has storm damage, file the claim yourself, get the insurance adjuster's assessment, then get independent quotes.

4. Their quote is 30%+ below everyone else's. A dramatically lower quote almost always means they're cutting corners somewhere — thinner underlayment, fewer nails per shingle, skipping ice and water shield, or planning to overlay instead of tear off. Ask them specifically where the savings come from. If they can't explain, they're not really saving you money — they're deferring the cost to your next roof.

5. No physical business address. A PO box or mail drop is not a business address. You want a contractor you can find if something goes wrong in year 3 of a 10-year workmanship warranty.

These are the questions that separate informed homeowners from easy targets. Ask all of them — a good contractor will answer without hesitation:

1. "Can I see your license/registration number?" And then verify it yourself. Takes 5 minutes.

2. "Who will actually be on my roof — your crew or subcontractors?" Some companies are just sales operations that sub out all the work. You want to know who's doing the labor.

3. "What brand and product line of shingles will you use?" Not just "architectural shingles" — the specific manufacturer and product. This is what the warranty is tied to.

4. "Do you pull permits, and is the cost included?" Most NY/CT towns require a permit for roof replacement. The contractor should handle this, and the cost should be in the quote.

5. "Can I see photos of recent work?" Or even better, "Can I talk to a homeowner you worked for in the last 6 months?" Reviews online are helpful but can be gamed. A reference call is harder to fake.

6. "What happens if you find rotted decking?" This is the most common add-on cost in roofing. Good contractors will quote a per-sheet price upfront (typically $75-150 per 4x8 sheet of plywood) so you know the cost before they find it, not after.

7. "What does your warranty cover, and what does it NOT cover?" Make them explain the limits. A warranty that excludes "acts of God" or "normal wear and tear" may not cover the scenarios you're actually worried about.

In the NY/CT area, roofing season runs from April through November. The best time to schedule is late spring (April-May) or early fall (September-October):

Why spring/fall is best: Temperatures between 50-80°F are ideal for asphalt shingle installation. Shingles need heat to seal properly — too cold and the adhesive strips don't bond. Too hot and shingles become soft and easily damaged during installation.

Why you should avoid peak summer: July and August are when roofers are busiest. You'll wait longer for quotes, longer for scheduling, and have less negotiating power on price. Booking in April or September often gets you the same crew at a better price with faster turnaround.

The worst time: December through February. Emergency repairs can and should be done, but a full replacement in winter is risky. Cold temperatures prevent proper sealing, snow and ice create safety hazards, and the work takes longer. If your roof can wait until spring, it should.

How far ahead to plan: Most reputable roofers book 2-4 weeks out in shoulder season, 4-8 weeks in peak summer. Start getting quotes at least 6 weeks before you want the work done.