By Thomas Construction · Connecticut roof replacement

See what a new roof costs on your house in about 10 minutes.

Your roof outlined from above, three options with real price ranges, and an install week you can reserve online. A technician confirms the final price before you sign anything.

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.

Zach Thomas Caldwell, OwnerYann Luc Sylvester, Head of Sales & Marketing

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

  • Veteran-owned
  • Licensed & insured
  • No salesperson visits
  • We never sell your information

Why homeowners use us

Buying a roof usually means booking an appointment just to learn the price, then trying to compare proposals that don’t line up.

It’s hard to tell what’s included, what could change once the old roof comes off, and when the work would actually happen.

Here you see the price first, on your actual roof, with what’s included and what could change spelled out, and you decide on your own time.

A simpler way to buy a roof

How it works

  1. 1

    Enter your address

    We outline your roof from aerial data and town records.

  2. 2

    See three real options

    Answer a few questions and see price ranges for your actual roof, with financing if you want it.

  3. 3

    Pick a week and reserve it

    Choose an install week and hold it with a $250 deposit that’s fully refundable until the day we come out.

  4. 4

    Confirmed, then scheduled

    A technician checks what satellites can’t see and confirms your final price. You review it and the contract before any work begins.

Every step, in detail →

What you’ll see

Your estimate looks like this, for your roof

Three options with real price ranges, what each one includes, and how much damaged decking is already covered. This one is an example. Yours is measured from your own roof.

Example estimate

Two-story colonial

about 2,300 sf of roof, 7/12 pitch

  • Essential

    Architectural shingles

    $18,500–$22,200

    • Full tear-off down to the deck, no overlays
    • Architectural shingles
    • Ice & water shield at eaves, valleys and penetrations
    • Synthetic underlayment

    3 damaged decking sheets included

  • CoreOur recommendation

    Architectural shingles

    $20,300–$24,400

    • Everything in Essential
    • Ice & water shield over the whole roof
    • Ridge vent upgrade
    • All new pipe boots and vents

    5 damaged decking sheets included

  • Complete

    Designer impact-rated shingles

    $25,700–$30,900

    • Everything in Core
    • Designer impact-rated shingles, premium colors
    • New gutters and guards
    • Skylight replacement

    8 damaged decking sheets included

Computed by our pricing engine on 2026-09-14 from pricing table v1. Ranges assume one existing layer of shingles and a standard install week.See yours

What you get

Plan-First Roofing

Plan-First Roofing is how Thomas Roofing replaces roofs in Connecticut: before anything comes off your house, you see your roof measured, your options with real price ranges, what could change the price and what each change costs, and the install week you reserve. A technician confirms the plan on site before you sign, and you get a Roof Record of the finished work.

What Plan-First Roofing means →
  • A price range on your actual roof

    From aerial measurement and town records, in about a minute.

  • Reserve your install week online

    A $250 deposit holds your week and your estimate. It’s fully refundable until the day a technician comes out, and goes toward your roof from then on.

  • Your final price after one short visit

    A technician confirms what satellites can’t see. If anything changes the price, you see it before you sign and before any work begins.

  • A real install window you choose

    Winter windows cost less because our crews are less busy then. You keep the difference.

  • No salesperson, ever

    No in-home presentation, and no price that vanishes at midnight. Questions by text, or a call if you want one.

  • Written workmanship warranty

    A 2-year workmanship warranty on every option, in writing, on top of the manufacturer warranty that comes with your shingles.

  • Clean-site guarantee

    Magnetic nail sweep at the end of every job, photo-documented.

Who’s behind Thomas Roofing

Built by Thomas Construction

Thomas Construction was founded on a frustration many Connecticut homeowners know well: too many contractors overpromise, communicate poorly and disappear when the work gets hard. Owner Zach Thomas Caldwell set out to build the opposite, a company defined by discipline, accountability and craftsmanship.

In more than 15 years in the trade, Thomas Construction has completed hundreds of projects across Connecticut as a full-service design-build contractor: detached and car-collector garages, barns, post-and-beam buildings, additions, ADUs and outdoor living spaces.

A new roof is a big, unfamiliar purchase, and it’s exactly where that frustration shows up. So Thomas Roofing brings the same standard to it: your price up front on your actual roof, a technician who confirms it before you sign, specialist roofing crews, and one accountable company from the first estimate to the final cleanup.

The name on the truck is a name we stand behind. That’s what Trust in Thomas means.

Who you’ll be dealing with

  • 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

Our story →

Questions people ask first

Can you really price a roof without seeing it?+

We measure it from aerial data and town records, which gets the size and pitch right for most homes. What aerial data can’t see, like how many layers are underneath or the condition of the deck, is why you see a range. A technician confirms the final price at a verification visit, before you sign anything.

What if there’s rot under the shingles?+

Every option includes an allowance for replacing damaged decking. If the verification visit finds more than the allowance covers, we photograph it and price it per sheet. You see the final number before you sign and before any work starts.

Why is the winter price lower?+

Our crews are less busy from January to March, and keeping them working costs us less then. We pass that difference to you. It’s a real cost difference, not a sale.

Do I have to decide today?+

No. Reserve a week or don’t. A window’s price can change as the window fills, and your deposit is fully refundable until the day we come out.

What if I want to talk to someone?+

Text us or call anytime. A real person reads every message, and nobody will come to your house to pitch you.

Do you offer financing?+

Yes, through HFS Financial. You can see what you qualify for in about a minute with a soft credit check that won’t affect your credit score. The loan is paid to you, so you pay for your roof the usual way, and there’s no prepayment penalty.

More questions →

See your roof, your options and your price.

Get My Roofing Estimate