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Asphalt shingle roof replacement

GAF shingle roofs for Milford and coastal Connecticut.

Full tear-off, GAF Timberline shingles, and your choice of three packages. Most roofs are done in one day.

5.0 on Google (23 reviews)GAF Certified ContractorLicensed & insured · HIC #0701539Most roofs done in one day

The short answer

Architectural shingles are the right roof for most Connecticut homes.

They handle our winters, look right on Capes, colonials and ranches, and cost far less than metal or slate. We install GAF Timberline shingles, the most widely installed shingle line in North America, as a full system: leak barrier, synthetic underlayment, starter strip, shingles and ridge cap, all GAF.

  • Full tear-off down to the decking on every job
  • Ice & water shield at the eaves and in valleys
  • Starter strip at both eaves and rakes
  • New flashing details and ventilation checked
  • Magnetic nail sweep and full cleanup the same day
Drone view of a blue Cape-style home with a new light gray architectural shingle roof

Best · Better · Good

Three roof packages. One honest estimate.

Every estimate shows all three side by side so you can choose. We don’t list a price here because no two roofs are the same. Size, slope, layers, decking and the materials you pick all change the number.

Best

Thickest shingle and premium components

Shingle
GAF Timberline UHDZ
Underlayment
GAF Deck-Armor breathable
Ridge cap
GAF TimberTex premium
Leak barrier
Ice & water shield at eaves and valleys
Starter strip
Eaves and rakes

Priced on your roof’s size, slope and materials.

Most popular

Better

Our most popular package

Shingle
GAF Timberline HDZ
Underlayment
GAF Tiger Paw premium synthetic
Ridge cap
GAF Seal-A-Ridge
Leak barrier
Ice & water shield at eaves and valleys
Starter strip
Eaves and rakes

Priced on your roof’s size, slope and materials.

Good

Solid protection at the lowest cost

Shingle
GAF Timberline HDZ
Underlayment
GAF FeltBuster synthetic
Ridge cap
GAF Seal-A-Ridge
Leak barrier
Ice & water shield at eaves and valleys
Starter strip
Eaves and rakes

Priced on your roof’s size, slope and materials.

Every package: full tear-off, GAF System Plus Limited Warranty, 5-year workmanship warranty, magnetic nail sweep and full cleanup.Get my three-option estimate

Backed in writing

Two warranties on every new roof

As a 2026 GAF Certified Residential Roofing Contractor, we can register your roof for GAF’s System Plus Limited Warranty. Our own workmanship warranty sits on top of it.

GAF

System Plus Limited Warranty

Covers the GAF roof system on qualifying installs when GAF shingles are paired with GAF accessories like starter strip, leak barrier and ridge cap. Only certified contractors can offer it.

5 yr

Charter Oak workmanship warranty

If something we installed fails because of how we installed it, we come back and fix it. In writing, with your contract.

FAQ

Shingle roof questions

What shingles does Charter Oak Roofing install?

GAF Timberline HDZ architectural shingles are our standard, and GAF Timberline UHDZ is our premium option. Both come in a wide range of colors.

How much does an asphalt shingle roof cost?

It depends on your roof's size, slope, number of layers, decking condition and the package you choose. We measure your roof and give you a free written estimate showing Best, Better and Good prices side by side.

How long does a shingle roof replacement take?

Most homes are done in one day. Steep, large or multi-section roofs can take two.

Do you tear off the old roof or roof over it?

We do a full tear-off on every replacement so we can inspect and repair the decking underneath. That is also required for the GAF System Plus warranty.

What happens if the plywood decking is rotted?

We replace damaged decking as we go. Your estimate states how many sheets are included and the per-sheet price for any extra, so there are no surprises.

What is ice and water shield and where does it go?

It's a self-sealing leak barrier. We install it along the eaves, where ice dams form, and in the valleys, per Connecticut code.

Free estimate

Get your free, written roof estimate

Tell us a little about your roof and we’ll call you back, usually within the hour during business hours. No pressure and no obligation. Ask about financing options.

Call or text
(203) 736-7739
License
CT HIC #0701539

Prefer to talk? Call (203) 736-7739. Licensed & insured, CT HIC #0701539.

Call nowFree estimate