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★★★★★ 4.9/5 from 405+ reviews

Professional Cheshire Roof Repair & Replacement. Free Estimates

23+ years protecting Cheshire homes and businesses. Same-day estimates. Manufacturer warranties up to 50 years.

📞 (877) 349-1553
23+
Years
500+
Projects
4.9
Rating
23+
Years Experience
500+
Projects Completed
4.9
Star Rating (405+ Reviews)
Licensed & Insured

Our Services

Our Roofing Services

Professional Roofing solutions for residential and commercial properties in Cheshire.

roof replacement
FREE ESTIMATE

Roof Replacement

A roof replacement in Cheshire typically runs $8,500 to $24,000 depending on the size and pitch. We give you an exact number upfront with a written proposal. No surprises on install day.

roof repair
SAME-DAY

Roof Repair

Missing shingles, cracked flashing, a leak over the kitchen. Whatever it is, we fix it. Our Cheshire repair crew runs 6 days a week. Most repairs take half a day.

storm damage repair
LICENSED

Storm Damage Repair

Storm damage claims in Connecticut have a 1-year filing window with most carriers. Don't wait. We'll inspect your roof, document the damage, and help you file before the deadline. If there's no damage, we'll tell you that too.

new roof installation
TOP RATED

New Roof Installation

New roof installation on new construction means getting the ventilation right from the start. We calculate intake and exhaust requirements based on attic square footage and install the right combination of soffit vents and ridge vent. Saves you money on cooling bills in Connecticut.

metal roofing
GUARANTEED

Metal Roofing

Corrugated metal and R-panel are cost-effective options for barns, detached shops, and covered patios in Cheshire. We install 29-gauge and 26-gauge corrugated with exposed fasteners using neoprene washer screws. For homes, we recommend 24-gauge standing seam with concealed fasteners. Cleaner look, no exposed fastener maintenance. DaVinci composite shake and slate profiles give you the metal longevity with a traditional Connecticut aesthetic.

shingle roofing
INSURED

Shingle Roofing

We install asphalt shingles from every major manufacturer. GAF, Owens Corning, CertainTeed, Atlas, Tamko, Malarkey, IKO. Each has different warranty tiers and price points. We walk you through the comparison without pushing one brand.

flat roofing
FREE ESTIMATE

Flat Roofing

PVC roofing membrane for Cheshire restaurants, commercial kitchens, and any rooftop near grease exhaust. PVC resists animal fats and chemical exposure that destroys TPO and EPDM. We install IB Roof Systems and Duro-Last PVC with heat-welded seams and custom-fabricated accessories. Built-up roofing (BUR) with 3-4 plies of fiberglass felt in hot asphalt is still the longest-proven flat roof system with a 30+ year track record in Connecticut.

commercial roofing
SAME-DAY

Commercial Roofing

TPO is our most-requested commercial membrane in Connecticut. Reflective, energy-efficient, and it welds together at the seams for a watertight bond. We install 60-mil and 80-mil systems with 15-20 year manufacturer warranties.

gutter installation
LICENSED

Gutter Installation

Improperly sized gutters cause fascia board rot and foundation erosion. We calculate gutter capacity using the rainfall intensity formula: roof square footage x pitch factor x rainfall rate (inches/hr for Cheshire). Standard 5" K-style handles 5,520 sq ft of effective roof area. Bigger roofs or steeper pitches need 6" gutters with 3x4" downspouts. We hang with hidden hangers screwed into rafter tails every 24".

roof inspection
TOP RATED

Roof Inspection

Our 27-point roof inspection covers: shingle condition, granule loss, nail pops, lifting tabs, ridge cap integrity, valley flashing, step flashing at walls, drip edge, pipe boot seals, vent function, soffit ventilation, gutter pitch, downspout capacity, fascia condition, decking (from attic if accessible), and visible signs of moisture in the attic. Written report with photos emailed same day.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Storm damage, fallen trees, sudden leaks. We handle all roofing emergencies in Cheshire. First we stop the water, then we fix the cause. Emergency response available 7 days a week.

skylight installation
INSURED

Skylight Installation

We install, replace, and repair skylights in Cheshire homes. Fogged glass, cracked frames, persistent leaks around old skylights. We fix it all. Sometimes replacing a 20-year-old skylight is cheaper than trying to repair it.

Ready to Get Started?

(877) 349-1553

Free Estimates • Available 24/7 • Licensed & Insured

Why Choose Cheshire Roofing & Maintenance?

Trusted by homeowners and businesses across Cheshire.

Financing Available

A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.

Written Warranty

Manufacturer warranty plus our workmanship warranty in writing. If something fails because of our installation, we come back and fix it at no charge. Period.

Manufacturer Certified

GAF Master Elite, Owens Corning Preferred, CertainTeed SELECT ShingleMaster. We carry certifications from the big three. That means factory-trained crews and the best available warranties.

23 Years in Cheshire

We've been roofing Cheshire homes since before half these companies had a website. 23 years means we know the local codes, the weather patterns, and the materials that hold up here.

Our Work

Recent Projects

View All Projects →

Simple Process

How It Works

1

We Inspect First

Free 27-point inspection covering every component of your roofing system. Photos shared with you on the spot. No obligation to hire us. The information is yours.

2

Written Estimate

Our Cheshire estimator builds your proposal same-day in most cases. Includes material options, warranty comparison, and a realistic timeline for your specific roof.

3

Installation Day

Crew shows up on time with all materials pre-staged. Tarps go down, old roof comes off, new roof goes on. Most Cheshire homes are done in a single day.

4

Your Approval

You see the finished roof, approve the work, and we register your manufacturer warranty on the spot. Written workmanship warranty handed to you at the walkthrough.

Verified Reviews

What Our Customers Say

★★★★★ 4.9/5 from 405+ reviews
★★★★★

"Got three quotes for a roof replacement. Cheshire Roofing & Maintenance was the middle price but the only one who actually got on the roof and showed me photos. Everyone else just eyeballed it from the driveway."

J
Jennifer U.
Cheshire
★★★★★

"Had them install a ridge vent to replace the old box vents. Attic runs about 15 degrees cooler now. Should've done it when we got the roof but better late than never."

D
Dave F.
Cheshire
★★★★★

"Our roof was 22 years old and starting to curl. They did a full tear-off and installed Timberline HDZ in Weathered Wood. Looks incredible. Crew was fast and cleaned up everything."

L
Lisa V.
Cheshire

Service Areas

Areas We Serve

Cheshire Roofing & Maintenance serves Cheshire and the surrounding communities. If you're within 30 miles, we'll come to you.

Farmington Litchfield New Milford Pine Meadow Shelton Torrington Wilton Branford Cromwell Gales Ferry

FAQ

Frequently Asked Questions

Yes. We offer 12-month same-as-cash, low-interest plans up to 144 months, and no-money-down options through GreenSky and Hearth. Credit approval takes about 5 minutes. A new roof is a major expense. Financing lets you get it done now without draining your savings.

There's no single "best" shingle. It depends on what you need. For warranty coverage, GAF Timberline HDZ with Golden Pledge is the best in the industry. For wind resistance, Owens Corning Duration with SureNail locks down tight. For value, CertainTeed Landmark or IKO Cambridge give you solid performance at a lower price point. We carry all of them.

Yes. One day is standard for most residential jobs. We start early, work efficiently, and finish before dark. If your roof is larger than 40 squares or has a complex layout, it might push to day two. Either way, we seal everything watertight before we leave each night.

Here's the process: we inspect your roof for free, document any storm damage with photos, and help you file the claim. Your insurance company sends an adjuster. We meet them on-site and walk the roof together. If approved, we do the work at the agreed price. If the estimate seems low, we supplement it with additional documentation.

Poor ventilation causes premature aging. If your attic runs hot in summer and your shingles are curling at 15 years, bad ventilation is probably why. Missing shingles cause water intrusion and accelerate everything. We do a free inspection and give you a straight answer: repair, plan for replacement in 2-3 years, or replace now.

Have more questions? Call (877) 349-1553

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

Call Now — Free Estimate
📞 (877) 349-1553

★★★★★ 4.9/5 from 405+ Reviews  ·  Licensed  ·  Insured

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