The Best Roofing Contractors in Cheshire, CT

Compare the highest-rated roofing professionals in Cheshire, Connecticut. All contractors are licensed, insured, and verified through our rigorous screening process.

#1

Cheshire Premier Roofing & Exteriors

4.8
(142 reviews)
Verified

A leading full-service roofing contractor serving Cheshire and surrounding areas. They specialize in high-quality residential and commercial roof replacements, using premium materials from GAF and CertainTeed. Their team is highly experienced in navigating insurance claims for storm damage and offers 24/7 emergency tarping and repair services. Known for meticulous craftsmanship and exceptional customer service.

1120 South Main Street, Cheshire, CT 06410

Specialties & Features

Storm Damage Restoration
Insurance Claim Assistance
Asphalt Shingle Systems
Emergency Repair
Commercial Flat Roofing

Business Information

Years in Business:18 years
Licensed:Yes
Insured:Yes
#2

New England Roofing & Siding Contractors

4.6
(118 reviews)
Verified

A well-established, family-owned roofer with deep roots in the Cheshire community. They offer a comprehensive range of services from minor repairs and preventative maintenance to complete roof overhauls. They are experts in dealing with the specific challenges posed by Connecticut's climate, including heavy snow loads, ice dams, and wind damage. They provide free, detailed inspections and clear estimates.

845 Highland Avenue, Cheshire, CT 06410

Specialties & Features

Residential Roof Repair
Ice Dam Prevention & Removal
Roof Maintenance Programs
Tile & Slate Roofing
Soffit & Fascia

Business Information

Years in Business:25 years
Licensed:Yes
Insured:Yes
#3

Connecticut Metal Roofing Specialists

4.7
(96 reviews)
Verified

As the name implies, this provider is a niche expert in metal roofing systems for both homes and businesses. They are the go-to contractor in Cheshire for standing seam, metal shingle, and corrugated metal roof installations. Their products are ideal for New England weather, offering superior durability against snow, ice, and high winds. They also handle asphalt shingle projects and are known for their efficiency and clean job sites.

322 Maple Avenue Unit 4, Cheshire, CT 06410

Specialties & Features

Metal Roof Installation
Energy-Efficient Roofing
Long-Lasting Roof Systems
Commercial Metal Roofs
Weather-Resistant Installation

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes

Why These Are the Top Roofing Contractors in Cheshire

The roofing market in Cheshire, CT, is driven by the region's four-season climate, which includes heavy winter snow, spring nor'easters, and summer thunderstorms. These conditions lead to common issues like ice dams, wind-lifted shingles, and water damage. Homeowners and businesses prioritize contractors with expertise in durable, weather-resistant materials and storm damage restoration. The market is competitive with a mix of long-standing local companies and larger regional operators, all of which must be well-versed in Connecticut building codes and insurance processes. High-quality workmanship and strong warranties are key decision-making factors for local customers.

High Ratings

4.7+ star average from verified customer reviews

Fully Licensed

All contractors are properly licensed and insured

Proven Experience

10+ years average experience in the industry

Local Experts

Familiar with Cheshire regulations and climate

Frequently Asked Questions About Roofing in Cheshire

Get answers to common questions about roofing services in Cheshire, Connecticut.

1What is the typical cost range for a full roof replacement on a Cheshire home?

For a standard asphalt shingle roof on a typical 2,000-2,500 sq. ft. Cheshire home, homeowners can expect a cost range of $12,000 to $25,000. This range depends on roof complexity, material choice (e.g., architectural shingles, metal), and the cost of complying with Connecticut's building codes, which require high-wind rated installation. Always get 3-4 detailed, written estimates from local, licensed contractors for an accurate price.

2When is the best time of year to schedule a roof replacement in Cheshire, CT?

The ideal windows are late spring (May-June) and early fall (September-October). These periods typically offer the dry, mild weather needed for safe installation and proper sealing of materials. Scheduling in summer is possible but can be hotter for crews, while winter installations are risky due to ice, snow, and cold temperatures that can compromise adhesive seals on shingles.

3Are there specific local permits or regulations in Cheshire I need to be aware of for a roofing project?

Yes. The Town of Cheshire Building Department requires a building permit for a full roof replacement. Your roofing contractor should typically pull this permit. The work must comply with the Connecticut State Building Code, which includes specific requirements for ice and water shield in valleys and at eaves, and high-wind nail patterns to withstand our New England nor'easters.

4How do I choose a reliable roofing contractor in the Cheshire area?

Prioritize contractors who are licensed in Connecticut, carry both liability and workers' compensation insurance, and have a strong local reputation. Ask for references from recent jobs in Cheshire or nearby towns like Southington or Wallingford, and verify they are familiar with local building department procedures. Be wary of storm-chasing companies that appear after major weather events.

5What are the most common roofing problems you see on older homes in Cheshire?

The most frequent issues are ice dam damage from winter freeze-thaw cycles, wind-driven rain infiltration from nor'easters, and general wear from our humid summers and snowy winters. We also often find inadequate attic ventilation in older colonials and capes, which accelerates shingle deterioration and contributes to ice dams. Regular inspections every 2-3 years are key to catching these local issues early.