Top 3 Roofing Contractors in Chester

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

#1

Chester Valley Roofing & Restoration

4.8
(127 reviews)
Verified

A premier full-service roofing contractor specializing in both residential and commercial projects. Known for exceptional craftsmanship and expertise in handling insurance claims for storm damage. They use high-quality materials and offer comprehensive warranties.

112 Main Street, Chester, MA 01011

Specialties & Features

Storm Damage Restoration
Insurance Claims
Asphalt Shingles
Emergency Tarp-Ups
Full Roof Replacements

Business Information

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

Berkshire Mountain Metal Roofing

4.7
(94 reviews)
Verified

Specialists in durable metal roofing systems ideal for Chester's heavy snow loads and variable climate. They also expertly handle slate and tile repairs. Renowned for their meticulous installations, historical home expertise, and long-lasting results.

445 Berkshire Trail, Chester, MA 01011

Specialties & Features

Metal Roofing
Slate & Tile Roofing
Snow Load Management
Historical Restoration
Roof Inspections

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes
Call Now
#3

Pioneer Valley Roofing Contractors

4.5
(112 reviews)
Verified

A reliable, family-owned roofer providing a wide range of residential services with a strong focus on repairs and maintenance. They are a trusted local provider for emergency leak repairs and routine inspections to prevent weather-related damage.

77 Middlefield Road, Chester, MA 01011

Specialties & Features

Roof Repairs
Leak Diagnosis
Preventative Maintenance
Gutter Systems
Emergency Services

Business Information

Years in Business:22 years
Licensed:Yes
Insured:Yes
Call Now

Why These Are the Top Roofing Contractors in Chester

The roofing market in Chester, MA, is heavily influenced by its New England climate, characterized by significant snowfall, ice dams, and occasional severe storms. This creates a high demand for durable, weather-resistant roofing materials (like metal and high-quality asphalt) and contractors skilled in storm damage restoration, ice dam prevention, and handling complex insurance claims. Local building codes also emphasize structural integrity for snow load capacity.

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 Chester regulations and climate