For Connecticut homeowners with an older roof

Not sure your roof has another Connecticut winter left? 7 signs to check this weekend.

Nothing’s leaking yet, but the roof is getting older and you’ve started to wonder. Here’s how to tell how much life is left, and how to see what a replacement would cost without inviting a salesperson over.

Zach Thomas Caldwell, OwnerYann Luc Sylvester, Head of Sales & MarketingFrom the Thomas Roofing team · October 2026

Why we ask: your address lets us find your roof in aerial imagery and town records and measure it. No one comes to your house unless you ask, and we never sell your information.

Rather talk to someone first? Call (860) 710-5862

If you’re reading this, it probably sounds like this

  • “It isn’t leaking, so maybe it has a few more years in it?”
  • “I have no idea what a new roof even costs anymore.”
  • “I don’t want to spend a Saturday with three salespeople just to find out.”
  • “I’d rather do it on my schedule than in an emergency.”

That last one is the right instinct. A roof replaced on your schedule usually costs less than one replaced after a leak picks the date for you: no water damage to fix, and you can choose a lower-priced week.

7 signs your roof is near the end

Grab binoculars and a flashlight. You can check most of these from the yard and the attic in half an hour.

  1. Shingles curling or cupping

    As shingles age they dry out, and the edges curl up or the middles cup down. Curled shingles catch the wind and let water under.

    How to check: Look along the roof in low morning or evening light, when edges that don’t lie flat cast shadows.

  2. Granules piling up in the gutters

    The granules protect the asphalt from the sun. When they wash off steadily, the shingles dry out and crack faster.

    How to check: A layer of sandy grit at the bottom of the downspouts.

  3. Bald or dark patches

    Spots where the granules are gone show the asphalt underneath. Those areas wear through first.

    How to check: Patches that look darker or smoother than the rest of the roof.

    Ready to see your number?

    See what a new roof costs on your house, from aerial measurement, before anyone comes out.

    Get My Roofing Estimate
  4. Cracked or missing shingles

    Brittle shingles crack in cold snaps and break off in wind. A few after a big storm can happen to any roof. A few every year means the roof is giving up.

    How to check: Pieces of shingle in the yard, or gaps you can see from the ground.

  5. Daylight or stains in the attic

    From inside, a worn roof shows itself as light through the boards, dark water stains on the wood, or damp insulation.

    How to check: Go up with a flashlight on a sunny day, and again after rain.

  6. A roofline that dips

    A sagging section means the deck or the framing under it has weakened, usually from moisture over years. It needs attention before the winter snow load.

    How to check: Look along the ridge from the street. It should be straight.

  7. Its age

    Asphalt shingle roofs in Connecticut commonly last about 20 to 30 years, depending on the shingle, the attic ventilation and how much sun the roof gets.

    How to check: Check your purchase paperwork or the town’s permit records for the last re-roof.

More on roofs over 20 years old →

Replace it now, or give it a season?

Probably fine for a season

  • One or two of these signs, on a roof under 15 years old
  • Nothing showing in the attic
  • Shingles still lie flat

Time to plan the replacement

  • Three or more of these signs
  • Any water or daylight in the attic
  • A roof over 20 years old, or a letter from your insurer about it

Either way, knowing the number now means you decide on your timeline.

Why planning beats waiting

about $1,150

less for a January install week than a standard week, on a typical two-story colonial with our current pricing

  • You pick the week

    Plan ahead and you choose when the crew comes. Wait for a leak and the leak chooses.

  • Winter weeks cost less

    Our crews are less busy from January to March, so those weeks are priced lower. It’s a real cost difference, not a sale.

  • No water damage on the bill

    A roof replaced before it leaks doesn’t come with rotted decking, stained drywall or wet insulation to fix too.

  • Insurers watch roof age

    Many insurers review roofs at around 15 to 20 years. Knowing your number now means a letter from them isn’t a surprise.

Seeing the price takes minutes and commits you to nothing.

How it works

How it works, on your schedule

  1. 1

    See your roof and your price in minutes

    Enter your address. We measure your roof from aerial imagery and town records and show you three replacement options with real price ranges. Nobody needs to come to the house for this part.

  2. 2

    Compare three options side by side

    Essential, Core and Complete, each with what’s included, the decking it covers and a real price range, so you can weigh them without anyone at your kitchen table.

  3. 3

    Reserve a week that suits you, or don’t

    Hold an install week online with a deposit that’s refundable until the day a technician comes out, or come back when you’re ready.

  4. 4

    A technician confirms the final price

    If you go ahead, a technician checks what aerial imagery can’t see, like the decking, the flashing and how many layers are up there, and confirms your final price before you sign anything.

Who you’ll be dealing with

The people behind your roof

Thomas Roofing is run by Thomas Construction, a veteran-owned Connecticut contractor. These are the people behind it.

  • Zach Thomas Caldwell, Owner

    Zach Thomas Caldwell

    Owner

    A veteran and lifelong builder, Zach founded Thomas Construction and sets the standard for every roof we put on: done correctly, communicated honestly, and finished clean.

  • Yann Luc Sylvester, Head of Sales & Marketing

    Yann Luc Sylvester

    Head of Sales & Marketing

    Yann answers homeowners’ questions by phone and email and makes sure your price, your options and your next step are clear, so nobody has to come to your house to explain them.

Rather talk to someone first? Call (860) 710-5862

Questions people ask

How do I know how old my roof is?+

Check your purchase paperwork or the seller’s disclosure. Town building permits usually record re-roofs. If the roof was never replaced, it’s as old as the house, and our estimate shows the year built from town records.

Can you replace a roof in winter?+

Often, yes. Crews work on dry days and take extra care in the cold. If a week’s weather won’t allow a proper install, we call before your week to move the start, and your price stays the same.

Is the online price the real price?+

It’s a range based on your actual roof, measured from aerial imagery and town records. What aerial data can’t see, like a second layer of shingles or damaged decking, is why it’s a range. A technician confirms the final price before you sign.

Do I have to talk to a salesperson?+

No. You see your price online. If you go ahead, the person who comes out is a technician who checks the roof, not someone who pitches you. If you want to talk, call us.

Find out where your roof stands before winter.

Your roof, three options and real price ranges, in minutes. Decide on your own time.

Rather talk to someone first? Call (860) 710-5862

Get My Roofing Estimate