Cheshire, CT's Trusted Roofing & Siding Contractor Since 1986
- 40 Years in Business
- Owens Corning Preferred Contractor
- BBB A+ Rating
Years in Business
One of the oldest roofing companies 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.
Property Protection
We deploy our specialized Equipter 'Roofers Buggy' to catch debris and protect landscaping, plus thorough magnetic sweeps.
Licensed & Insured
CT Home Improvement Contractor license HIC.0565252. Full liability and workers' comp coverage.
Our Roofing & Exterior Services
From emergency leak repairs to complete architectural shingle replacements, we handle every Connecticut exterior project with 40 years of trusted local craftsmanship.
Roof Replacement
Complete tear-off & architectural shingle replacement rated for 110–130 mph winds. Done in 1–2 days with magnetic sweep cleanup.
Get Free Quote →New Roof Installation
New construction & home additions engineered to Connecticut building codes with mandatory ice & water barrier protection.
Get Free Quote →Roof Repair & Inspections
Emergency leak detection, storm damage, chimney flashing, pipe boots & missing shingles. Honest photo proof with zero upsell pressure.
Get Free Quote →5" Seamless Gutter Replacement
Custom 5" seamless aluminum gutters extruded on-site with heavy-duty hidden screw hangers pitched for CT downpours.
Get Free Quote →Englert MicroGuard™ Gutter Guards
Heavy-duty Englert MicroGuard aluminum leaf defense keeps out pine needles, leaves & roof grit. End ladder cleanings permanently.
Get Free Quote →Gutter Cleaning & Flush
Hand debris cleanout, downspout pressure flush, and fascia inspection. Bagged and hauled away leaving lawns spotless.
Get Free Quote →Vinyl Siding Contractor
Premium low-maintenance siding, insulated thermal backing & custom aluminum trim wrap that eliminates painting for decades.
Get Free Quote →Skylight Installation
Certified Velux skylights and replacement units with multi-layer engineered step flashing that stay 100% leak-free in winter.
Get Free Quote →Why New Haven County Homeowners Have Trusted Kelley Since 1986
One of the Oldest Roofers 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. Verify our credentials on the Owens Corning Contractor Directory (Profile #248259) →
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. Supervised on-site by Jon using the Roofers Buggy debris 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 — Cheshire & Wallingford, CT
Before
After
Gutter replacement — Cheshire, CT
Before
After
Vinyl siding — Meriden, CT
Hear From Your Neighbors
"Kelley Roofing completed my parent’s new roof and gutters recently. They were exceptional to work with. From getting us a detailed quote to providing the warranty at the end, everything went smoothly and Jon or his staff got back to me immediately with answers to any questions. We are very happy with the roof and would highly recommend them."
"I had my roof done by Kelley Roofing four years ago and they did an outstanding job! Today I had an issue with my gutter and called them for assistance. They came right out to my house within ten minutes and fixed the issue. They are professional, courteous, and responsive. I highly recommend them for quality work, great service, competitive prices, and the utmost professionalism."
"My roof and gutters were replaced about 6 months ago by Kelley Roofing and they did a great job for lower price compare to other companies in around Cheshire. Fast, clean and professional! 5 star service! Will definitely recommend Kelley roofing for any roofing / gutters replacement."
"Jon and his crew replaced my asphalt shingles roof in Oct 2021, so I could install 28 solar panels over one side. The price was very competitive, and they completed removing and installing the new roof within a day, with attention to every details, leaving the yard spotless. The roof and panels haven't had any issues whatsoever over the last 20 months and look terrific. I couldn't be happier! Highly recommended."
"5-star experience with Kelley Roofing LLC. Prompt response, honest pricing, and quality craftsmanship from a trusted Cheshire exterior contractor."
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
Headquartered at 175 Cedar Ln in Cheshire, CT, Kelley Roofing has provided trusted residential roofing, siding, and gutter services across New Haven County for four decades. Jon Kelley is on every job site, delivering prompt inspections, direct personal oversight, and dependable craftsmanship backed by 40 years of local ownership.
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