You requested three quotes like everyone told you to. One came in at $12,000. Another at $18,500. The third? $27,000. Same roof. Same house. What's going on here?
If you're staring at wildly different roofing estimates wondering whether you're about to get ripped off—or whether the cheap guy is going to leave you with a leaky mess—you're not alone. This is one of the most common frustrations Connecticut homeowners face, and honestly, the confusion is by design.
Some contractors count on you not knowing what questions to ask.
We think that's wrong. So let's pull back the curtain.
The Real Reasons Roofing Quotes Swing by Thousands of Dollars
Before you assume the highest bidder is gouging you or the lowest is your lucky break, understand this: roofing estimates aren't comparing apples to apples. They're often comparing apples to oranges to something that might not even be fruit.
Here's what's actually driving those numbers apart:
Materials aren't created equal. A quote using builder-grade 3-tab shingles will look very different from one specifying architectural shingles with a 50-year warranty. Both are "shingles." One will be protecting your home long after the other has curled and cracked. The quote might just say "asphalt shingles" without telling you which.
Labor quality varies dramatically. Is the crew W-2 employees who've been trained and certified? Or day laborers pulled from a parking lot that morning? You won't see "subcontractor roulette" as a line item, but it's baked into that lower price.
Scope of work isn't standardized. One contractor includes tear-off, new underlayment, ice and water shield in the valleys, proper flashing, and hauling away the debris. Another "forgets" to mention they're just layering new shingles over your old ones—which most manufacturers won't warranty.
Overhead tells a story. A legitimate company carries insurance, workers' comp, proper licensing, and stands behind their work with real warranties. That costs money. A guy working out of his truck with a disconnected phone number next month? Less overhead. More risk for you.
7 Roofing Quote Red Flags
Click each item to learn why it's a warning sign
Quality contractors are booked out weeks or months in advance. Immediate availability often signals desperation, lack of other work, or a fly-by-night operation that won't be around when problems arise.
A professional estimate should detail materials, labor, permits, and warranty terms. If they can't tell you exactly what you're paying for, they either don't know—or don't want you to know.
Industry standard is a small deposit with the balance due at completion. Demanding 50% or more upfront is a classic setup for disappearing contractors. Your money leaves before the work arrives.
"We're on Google" isn't verification. Storm chasers blow into Connecticut after weather events, collect deposits, do shoddy work, and vanish. Find a local office you can actually visit.
"This price is only good until I walk out the door" is manipulation, not a deal. A company confident in their value gives you time to decide. Pressure tactics hide problems they don't want you to discover.
A "lifetime warranty" from a company that won't exist in five years is worthless paper. Ask who backs it, what it actually covers, and whether it's transferable if you sell your home.
Professionals focus on their own quality work, not tearing down others. Excessive negativity about competitors is often projection—and a sign they can't sell on their own merits.
Questions That Separate the Pros from the Problems
When a contractor hands you a quote, don't just look at the bottom line. Ask these questions and watch their reaction:
"Can you walk me through exactly what's included in this price—and what's not?"
A good contractor will patiently explain every line item. A shady one will get vague or defensive.
"Who will actually be on my roof—your employees or subcontractors?"
In-house crews mean accountability. Subcontractors mean the company you hired might not even meet the people doing the work.
"What happens if something goes wrong during the project or after?"
Listen for specifics. "We'll take care of it" is not an answer. A warranty process, a dedicated service contact, clear timelines—that's an answer.
"Are you licensed and insured, and can I see proof?"
This isn't rude. It's due diligence. Any legitimate contractor will hand it over without hesitation.
"Will you pull the permit, and will there be an inspection?"
Skipping permits saves the contractor time and money—and exposes you to liability, code violations, and insurance claim denials down the road.
What a Transparent Roofing Quote Actually Looks Like
Since we're in the business of answering questions others dodge, here's what you should expect to see broken down in any professional roofing estimate:
- Tear-off and disposal: Removing your existing roof and hauling it away properly
- Decking inspection/repair: Checking (and fixing) the plywood beneath your shingles
- Underlayment: The waterproof barrier that goes down before shingles
- Ice and water shield: Critical in Connecticut for preventing ice dam damage
- Shingles: Brand, product line, warranty length, and color
- Flashing: Metal pieces that seal roof penetrations and transitions
- Ventilation: Ridge vents, soffit vents—proper airflow extends roof life
- Cleanup and disposal: Debris removal, magnetic nail sweep of your property
- Permit fees: Yes, this should be included
- Warranty details: Both manufacturer and workmanship coverage
If your quote is missing half of these categories, you're not comparing full pictures.
"They went above and beyond!" — Donald V.
The Bottom Line
Wide-ranging roofing quotes aren't random. They're a symptom of an industry where some companies count on customer confusion to pad their margins or cut corners.
You don't have to play that game.
Get multiple quotes. Ask hard questions. Compare what's actually included. And trust your gut—if something feels off, it probably is.
If you want a roofing quote where everything is on the table, we're happy to provide one. No pressure. No games. Just the information you need to make the right decision for your home.
