This directory holds five roofing listings for Middlebury, Connecticut. None of them has a Google rating matched to it yet, so what follows is contact detail rather than reputation data.
Four of them are recorded in Naugatuck Valley County. The rest are in New Haven County. Roofing permits and inspections are issued locally rather than by the state, so a re-roof in Middlebury goes through Naugatuck Valley County or the municipality's own building department, whichever holds jurisdiction at the property.
Hiring a roofer in Middlebury: what this page knows
Connecticut does not license roofers; it requires them to register with the state, and that registration covers work in Middlebury. The Connecticut roofing license rules explain what a registration number does and does not tell you.
Connecticut's peak severe-weather season: Year-round, weighted to summer thunderstorms and winter storms. The Connecticut storm center lists any National Weather Service alert active right now.
We have not modeled a cost index for Middlebury. The national baseline puts a full roof replacement at $5,625–$27,000 and a repair at $250–$3,500; local labor, permit fees and access move both.
All Listings in Middlebury
5 listings
Roofers within 20 miles of Middlebury
Middlebury has 5 roofing listings of its own, shown above. 635 more listings are based in other towns within 20 miles. Below are the top 12, one card per company, ranked the same way as the list above: verified listings first, then by Google reviews, rating and name.
Each card names the town the business is based in and its straight-line distance from Middlebury. Being based nearby is not the same as working in Middlebury — ask whether they cover your address.
From their Google profile: Pro Exteriors was established by a team of industry professionals dedicated to providing the highest quality solutions.
From their Google profile: At CMW Roofing & Siding, we are proud to be your local residential and commercial roofing, siding, and gutter company.
From their Google profile: Flash Roofing LLC is your local roofing and exterior specialist, proudly serving Prospect, CT, and surrounding areas.
From their Google profile: Greenland Construction is Brookfield’s trusted partner for expert home improvements, specializing in roofing, siding, windows, doors, gutters, decks, railings, and skylights.
From their Google profile: Rob's Roofing LLC specializes in the repair, maintenance, and installation, as well as high-quality roofing systems.
Licensing for roofers working in Middlebury
Connecticut does not license roofing contractors. It requires them to register with the Connecticut Department of Consumer Protection, and that requirement covers work in Middlebury.
Registration and licensure are not the same thing — a registration number records that a business completed a filing, and it sits alongside, not instead of, a permit and an inspection through Naugatuck Valley County or the city.
Source: Connecticut Department of Consumer Protection. Checked August 2026. Licensing rules change — verify before you sign anything.
What roofing work costs
We have not modeled a cost index for Middlebury, so there is no Middlebury figure here. These are the national baseline bands, unadjusted.
National reference bands, not quotes and not local numbers. Local labor rates, permit fees and access all move them.
All roofing cost guidesOther Naugatuck Valley County towns with listings
Same county, same inspections department, same code — these are the other Naugatuck Valley County places this directory has roofers for.
Work out the job before you call
Roofing in Middlebury, CT: questions answered from the data
How many roofing contractors are listed in Middlebury, CT?
5 roofing listings are recorded at Middlebury, Connecticut addresses in this directory. The count is read from the directory's own database each time this page is rebuilt; a listing is a location record, and the list above shows one card per company.
Does Connecticut require a roofing license?
No — it requires registration instead. Connecticut does not license roofers; it requires them to register with the state, and that registration covers work in Middlebury. The Connecticut roofing license rules explain what a registration number does and does not tell you. You can check a credential on the Connecticut authority's own site.
How much does a roof replacement cost in Middlebury?
We have not modeled a cost index for Middlebury. The national baseline puts a full roof replacement at $5,625–$27,000 and a repair at $250–$3,500; local labor, permit fees and access move both. Nobody has priced your roof from this page; the only number worth planning around is a written quote from a contractor who has been on it.
When is storm season in Middlebury?
Connecticut's peak severe-weather season: Year-round, weighted to summer thunderstorms and winter storms. The Connecticut storm center lists any National Weather Service alert active right now. Season boundaries are National Weather Service climatology for the state, not a forecast for any one property.
Which county handles roofing permits in Middlebury?
Most listings on this page are recorded in Naugatuck Valley County, with some in New Haven County. Roofing permits and inspections are issued locally rather than by the state, so a re-roof in Middlebury goes through the county or the municipality's own building department, whichever holds jurisdiction at the property.