Cheshire, CT's Trusted Roofing & Siding Contractor Since 1986
- 40 Years in Business
- Owens Corning Preferred Contractor
- BBB A+ Rating
Years in Business
The oldest roofing company in New Haven County. We were here before your last two roofers even started.
Estimates & Inspections
No cost, no pressure. We visit your home, measure, photograph, and give you a straight price — in writing.
Financing Available
Need a new roof but not ready to pay in full? Flexible financing lets you start today. Learn more →
Licensed & Insured
CT Home Improvement Contractor license HIC.0565252. Full liability and workers' comp coverage.
Our Roofing & Exterior Services
From a single shingle repair to a full roof replacement, we handle every job with the same 40 years of expertise.
Roof Replacement
Full tear-off and replacement with premium shingles. Our #1 service — done in 1–2 days.
Get Quote →New Roof Installation
New construction roofing for builders and homeowners. Designed to spec from day one.
Get Quote →Roof Repair & Inspections
Leaks, storm damage, missing shingles. We find the problem and fix it — fast.
Get Quote →Gutter Replacement
Seamless aluminum gutters sized and pitched for your roofline. No more overflow.
Get Quote →Gutter Guards
Stop climbing ladders. Gutter guards keep leaves out and water flowing freely year-round.
Get Quote →Gutter Cleaning
Thorough cleanout, downspout flush, and visual inspection. Keeps your foundation safe.
Get Quote →Vinyl Siding
Durable, low-maintenance siding that transforms your home's curb appeal instantly.
Get Quote →Skylight Installation
Bring natural light into any room. Professional installation with leak-proof flashing.
Get Quote →Why New Haven County Homeowners Have Trusted Kelley Since 1986
The Oldest Roofer in the Area
Most of our competitors have been around less than 15 years. We've been re-roofing homes in New Haven County since 1986 — through every storm, every market cycle, every trend. Forty years of showing up and doing the job right.
Owens Corning Preferred Contractor
Kelley Roofing is a verified member of the Owens Corning Roofing Contractor Network — Preferred tier. That means our licensing, insurance, financial stability, and workmanship history have been reviewed and vetted. You can find us on the Owens Corning "Find a Contractor" locator.
Every Owens Corning roof we install is backed by the standard Owens Corning warranty — giving you the manufacturer's promise behind every shingle.
The Roofers Buggy: Our No-Mess Process
Most roofers leave your yard looking like a war zone. We use the Roofers Buggy system (from NewRoofNoMess.com) to contain debris, protect your landscaping, and leave your property spotless. It's roofing without the mess — and your neighbors will notice.
A+ BBB Rated · CT Licensed & Insured
Our A+ Better Business Bureau rating means accountability you can verify. We're fully insured with workers' compensation and carry CT Home Improvement Contractor license HIC.0565252 — as Connecticut law requires. Always ask your roofer for their license number. Here's ours.
Your New Roof in 3 Simple Steps
Free Inspection & Quote
We visit your home, measure your roof, photograph any damage, and give you a straight, honest price — in writing, with no surprises.
Pick Your Plan
Shingles, colors, timeline — we walk you through every option at your pace. No pressure, no upselling. You decide what's right for your home.
We Get to Work
Most roofs done in 1–2 days. Our crew uses the Roofers Buggy process so your yard is left spotless. You'll barely know we were there.
See the Difference
Real projects from your neighbors' homes across New Haven County.
Before
After
New roof — Hamden, CT
Before
After
Roof replacement — Wallingford, CT
Before
After
Gutter replacement — Cheshire, CT
Before
After
Vinyl siding — Meriden, CT
Hear From Your Neighbors
"[OWNER: Featured review — ideally one that mentions a specific crew member name, describes the cleanup/Roofers Buggy process, and names the town. Example: 'Mike and his crew replaced our entire roof in Cheshire in just a day and a half. They used that buggy system to catch all the debris — my flower beds looked exactly the same after as before. The price was fair, they showed up on time, and Mike walked us through every step. Best contractor experience we've ever had.']"
"[OWNER: Review #2 — short review from a homeowner mentioning quality, crew, or timeliness. Example: 'Fast, fair, and professional. Had our roof done in one day. Highly recommend Kelley Roofing.']"
"[OWNER: Review #3 — ideally a storm damage/insurance claim experience. Example: 'After the big storm, Kelley helped us with the insurance claim and had the roof replaced within a week. Couldn't have been easier.']"
"[OWNER: Review #4 — a gutter or siding review. Example: 'New gutters and gutter guards — the crew was polite, cleaned up everything, and the price was very reasonable.']"
Roof Now, Pay Later
[OWNER: financing partner name + terms, e.g. "Through GreenSky — 0% interest for 12 months" or "No payments for 12 months with approved credit"]
Don't let budget hold you back from a roof that protects your family. We offer flexible financing so you can get started today and pay on your schedule.
Explore Financing Options →Our Workmanship, Guaranteed.
Every Owens Corning roof we install is backed by the standard Owens Corning warranty — the manufacturer's commitment to quality materials. On top of that, you get Kelley's own workmanship guarantee, built on 40 years of standing behind every roof we put on.
When we put our name on a roof, we mean it. If something isn't right, we make it right — just as we have since 1986.
Proudly Serving New Haven County & Beyond
Based in Cheshire and serving every corner of New Haven County, plus nearby towns in Hartford and Middlesex counties.
…and all 27 New Haven County towns, plus Plainville, Berlin, Farmington, Durham, Middlefield & Cromwell.
Frequently Asked Questions
Most Connecticut homes fall in the $9,000–$18,000 range depending on roof size, pitch, and materials chosen. The only way to get an accurate number is a free on-site inspection — we measure, photograph, and give you a firm quote with no hidden fees.
Yes. We offer flexible financing options so you can get the roof you need today and pay over time with manageable monthly payments. Ask about current terms when you schedule your free inspection.
Absolutely. We've helped homeowners navigate storm-damage insurance claims for 40 years. We document the damage thoroughly, meet with your adjuster on-site, and make sure nothing gets overlooked in your claim.
Request a free storm-damage inspection → or call (203) 271-2926.
Most residential roofs are completed in 1–2 days. Larger or more complex roofs (steep pitch, multiple layers, dormers) may take a day longer. We'll give you a clear timeline during your free inspection so you know exactly what to expect.
We recommend architectural (dimensional) shingles rated for 110–130 mph winds with algae-resistant granules — built for Connecticut's freeze-thaw cycles and shaded lots. As an Owens Corning Preferred Contractor, we install durable Owens Corning architectural shingles and can walk you through the best options for your specific home.
Book a free consultation → or call (203) 271-2926.
Yes. Kelley Roofing LLC holds CT Home Improvement Contractor license HIC.0565252 and carries full liability insurance and workers' compensation coverage. Connecticut law requires all home improvement contractors to be licensed — always ask for the number. Ours is HIC.0565252.
Ready for a Worry-Free Roof?
Fill out the form and we'll reach out within one business day with a free, no-obligation quote. Or pick up the phone — we answer.
Or call to speak with our team directly