For Connecticut homeowners planning a replacement

Why a January roof can cost less than a May one, and whether winter works for your house.

Our crews are less busy from January to March, so those weeks are priced lower. That’s a real cost difference, not a sale. Here’s how winter installs work in Connecticut, when they don’t, and how to see your winter price.

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

  • “I know it needs replacing. I just don’t want to pay peak-season prices.”
  • “Can they even put a roof on when it’s cold out?”
  • “Every winter special I’ve seen looks like a gimmick.”
  • “I’d like it done before the spring rain, not after.”

Fair on every count. Here’s the straight version: why winter costs less, when it works, and when it doesn’t.

5 things to know about a winter roof in Connecticut

  1. Why it costs less

    January to March is the slow season for roofing crews. Keeping our crews working through it costs less than the spring rush, so those weeks are priced lower.

  2. Yes, roofs go on in winter

    Crews work on dry days, clear snow and ice before tear-off, and handle the stiffer shingles with more care. Days are shorter, so a job can take an extra day.

  3. Shingles still seal properly

    Adhesive strips need warmth to seal, so in the cold crews hand-seal shingles where the manufacturer calls for it.

    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. Bad weather moves the start, not the price

    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.

  5. Some roofs should wait for spring

    A steep, complicated roof, or a designer shingle that’s harder to handle in the cold, can be better in a spring week. Your technician will tell you.

The full guide to winter roofing in Connecticut →

Is winter right for your roof?

A good fit for winter

  • Your roof has another season in it and you want the lower price
  • You want it done before a spring insurance or sale deadline
  • A leak that shouldn’t wait for spring

Better in spring

  • A steep, complicated roof
  • Designer shingles that are harder to handle in the cold
  • No flexibility at all on the start date

Why look at winter weeks now

about $1,150

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

  • Week prices follow the calendar

    Our week prices move with how full the crew calendar is. As a winter week fills, its price can go up, so the lowest prices are on the weeks still open.

  • Your deposit stays refundable

    Holding a week takes a deposit that’s fully refundable until the day a technician comes out. Change your mind before then and you get it back.

  • Ready before spring rain

    A roof replaced in winter is ready for the heavy spring rain that finds every weak roof.

  • Checked before you sign

    A technician confirms the final price before you sign anything, winter week or not.

See your winter price on your actual roof in minutes. No winter special, just each week’s real price.

How it works

How to see your winter price

  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 weeks side by side

    After you pick an option, you see install weeks with their own prices, so you can see exactly what a winter week saves on your roof.

  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

Is the winter price a promotion?+

No. It reflects a real difference in what it costs us to run crews in the slow season, and it’s priced the same way for everyone. There’s no countdown and no code to enter.

What if it snows during my week?+

Crews clear snow and ice before tear-off when conditions allow. If the weather won’t allow a proper install, we call before your week to move the start, and your price stays the same.

How much does a winter week save?+

It depends on your roof and the week. On a typical two-story colonial with our current pricing, a January week is about $1,150 less than a standard week. Your estimate shows each week’s price for your actual roof.

See what a winter week costs on your house.

Your roof, three options and every install week’s price, in minutes.

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

Get My Roofing Estimate