Roofing services in Cheshire, CT

Trusted Roofing Services in Cheshire, CT

Roofing Cheshire homes the way we have since 2002 — measured on site, priced in writing, and finished the way we would want our own roof finished.

Licensed & Insured 4.5-Star Rated 24/7 Emergency Service Serving Cheshire
942+ Projects Completed
1,754+ Happy Customers
682+ 5-Star Reviews
24+ Years Experience

Roofing Services in Cheshire

From a single lifted panel to a full tear off, we handle every roofing job a Cheshire, CT home is likely to need.

Wind Damage Roof Repair

Missing shingles get matched as close as weathering allows. Loose metal gets new fasteners and washers, and the eaves, rakes and ridge get sealed back up tight.

Roof Coating

A coating buys real years on the right roof and wastes money on the wrong one. We will tell you honestly which kind you are looking at.

Storm Damage Roof Repair

We repair what the storm actually broke. If that is one slope, we do one slope, and we will not pad an estimate to make a claim look bigger.

Commercial Roofing

Churches, shops, barns and small commercial buildings. We have roofed everything from a wood shed to a steeple.

Roof Leak Repair

If two other people have caulked it and it still leaks, call us. Most stubborn leaks turn out to be flashing, a valley, or a fastener nobody thought to check.

Skylight Repair & Installation

Old skylights leak at the flashing long before the glass ever fails. We reflash, reseal, or set a new unit and tie it in properly.

Metal Roof Installation

This is the work our name is attached to. Two decades of tin roofs on houses, churches, barns and additions, installed by crews who cut the trim on site instead of forcing something that almost fits.

Gutter Guard Installation

Guards and screens so you are not up a ladder every fall digging pine needles out of the gutter by hand.

Roof Repair

Small repairs get the same crew and the same care as a full roof. Free estimate, a price in writing, and the work done before the next rain moves in.

Roof Replacement

Full tear off, decking checked board by board, then a new metal or shingle roof over proper underlayment. You get the price and the start date before anything comes off.

Slate & Tile Roof Repair

An older roof deserves to keep its character. We repair rather than replace wherever the material still allows it.

Soffit & Fascia Repair

Squirrels, wasps and water all treat a soft soffit as a front door. We close it up properly instead of patching over it.

Flat Roof Repair

Porch roofs, additions and low slope sections that hold water instead of shedding it. We rework the flashing, seal the seams, and get water moving again.

Metal Roof Repair

A twenty year old panel roof usually needs fasteners and sealant, not replacement. We refasten with new washers and get you another long stretch out of it.

Emergency Roof Repair

Storm damage does not wait for business hours. We get the opening closed, photograph it for your insurance, and put the real fix on the schedule.

Hail Damage Roof Repair

Repair or replace, we handle both, and we work from what the roof actually needs rather than from what an adjuster might approve.

Asphalt Shingle Roof Repair

A shingle repair should not be visible from the street. We match as close as the weathering allows and blend the new work into the old.

Roof Inspection

Inspections come free with an estimate. We would rather find the small problem this spring than replace a ceiling for you next winter.

Roof Waterproofing

The layer you never see is what keeps water out on the ugly days. We do not thin it out to save a few dollars on a bid.

Ice Dam Removal

Removing the ice is the easy half. We also look at ventilation and insulation so it stops happening every January.

Your Cheshire, CT Roofing Company

We have never charged for an estimate and we are not about to start. A Cheshire homeowner ought to be able to find out what a roof costs without buying a sales pitch first, so we measure, photograph what we find, and put a real number on paper.

What people tell us most often is that we told them the truth. Sometimes that truth is that the Cheshire roof they were ready to replace has another eight or ten years in it and only needs the valleys resealed.

Metal roof over the screened porch of a rustic cabin in Cheshire

Why Cheshire Homeowners Choose Us

A family roofing company that has kept the same habits since 2002.

Family Owned Since 2002

The same family started this company putting metal roofs on neighbors houses in 2002. It has never been sold, franchised or handed off to a call center.

We Leave the Yard Clean

Beds get covered, tear off gets hauled as we go, and a magnet goes over the drive before we pull out. Your yard should look like we were never there.

Colors You Pick Yourself

Around twenty standard metal colors, and the chart comes out with the estimate so you can hold it up against your siding and shutters before you commit.

Estimates Are Always Free

Somebody comes out, measures, gets on the roof, and leaves you a written price. No charge, no obligation, and no number that expires if you do not sign today.

We Show Up When We Say

You get a start date and we hold to it. If weather moves your job we call you, rather than leaving you watching the driveway.

Frequently Asked Questions

Wondering about metal versus shingle, or what a new roof runs in Cheshire? Start here.

Is a metal roof worth it for a Cheshire home?

For most Cheshire homes, yes. A metal roof costs more up front than shingles, but it usually outlives two or three shingle roofs, sheds rain and snow better, and does not peel off in a hard wind. We will price metal and shingle side by side so you can compare real numbers instead of guessing.

How long will a metal roof last on a house in Cheshire?

A metal roof installed properly on a Cheshire home should give you 40 to 60 years, and standing seam often goes longer because there are no exposed fasteners. Screws and sealants on a panel roof want attention around year 20, which is a small job next to a re-roof.

Can you repair my roof instead of replacing it in Cheshire?

Often, yes. Plenty of the Cheshire roofs we get called to look at need flashing reworked or a section refastened, not a whole new roof. We will tell you honestly which one you are looking at, and if it is repairable we would rather repair it.

What does a new shingle roof cost in Cheshire?

A typical Cheshire shingle roof runs roughly $8,000 to $18,000 in 2026 for an average single family home, and more if the deck has rot or the roof is steep and cut up with dormers. We do not price off a satellite photo — somebody comes out and measures.

How much does a metal roof cost in Cheshire?

Most Cheshire metal roof jobs land somewhere between about $12,000 and $30,000 in 2026, depending on square footage, pitch, panel type and how much tear off there is. Standing seam runs higher than exposed fastener panels. We measure before we quote, and the estimate is free.

Do you work with insurance after a storm in Cheshire?

We do. After a storm we photograph the damage on your Cheshire roof and write an itemized estimate you can hand to your adjuster. We do not file the claim for you and we will not promise you what an adjuster is going to approve — that is their call, not ours.

What Our Customers Say

What people say once the crew has packed up and gone home.

★★★★★

"New gutters and guards after they did our roof. No more climbing up there every October to dig out pine needles by hand."

— Amanda K.
★★★★★

"Thank you so much to the entire crew at Roofing Brothers for our amazing new tin roof! You were amazing to work with and I couldn't recommend you to others enough! Great communication, pricing, color options, efficiency, and HONESTY! If anyone needs a new roof, I highly recommend this crew! Phenomenal job."

— Kayla M.
★★★★★

"Tore off two layers of old shingles and found rotten decking underneath. They showed me the boards, told me what the change would cost, and let me decide before going ahead."

— Sherri N.

Nearby Cities We Serve

We take care of homeowners in these neighboring communities as well.

Find Us in Cheshire

Need a Roofer in Cheshire, CT?

Give us a call and we will come take a look. Estimates are always free anywhere we work in Connecticut.

(877) 509-1137 — Free Estimate