Top 3 Roofing Contractors in Cheshire

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

#1

Berkshire Roofing & Restoration

4.8
(127 reviews)
Verified

A premier full-service roofing contractor specializing in both residential and commercial projects. They are known for their expertise in handling complex insurance claims for storm damage and their meticulous installation process. They use high-quality materials from GAF and Owens Corning and offer strong warranties, including their own craftsmanship guarantee.

42 South Street, Cheshire, MA 01225

Specialties & Features

Storm Damage Restoration
Insurance Claims
Asphalt Shingles
Ice Dam Prevention
24/7 Emergency Services

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes
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#2

Cheshire Peak Roofing Contractors

4.6
(94 reviews)
Verified

A highly respected local roofer with deep roots in the community. They excel in roof replacements and repairs designed to withstand the harsh Berkshire winters, with a focus on proper ventilation and ice/water shield systems. They are a certified installer for certain metal roofing brands and offer elegant standing seam options alongside traditional asphalt.

1103 Main Road, Cheshire, MA 01225

Specialties & Features

Residential Roof Replacement
Metal Roofing Systems
Roof Ventilation
Historical Home Roofing
Maintenance Programs

Business Information

Years in Business:22 years
Licensed:Yes
Insured:Yes
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#3

Adams & Sons Roofing Services

4.5
(78 reviews)
Verified

A reliable, family-owned and operated business known for its honest assessments and high-quality repair work. They are a go-to for urgent leak repairs and maintenance, helping homeowners avoid major replacements. Their team is experienced with a variety of materials, including slate and tile, and they provide thorough post-storm inspections.

845 Cole Avenue, Unit B, Cheshire, MA 01225

Specialties & Features

Roof Repair & Leak Mitigation
Emergency Tarping
Slate & Tile Roofing
Roof Inspections
Gutter & Siding Integration

Business Information

Years in Business:18 years
Licensed:Yes
Insured:Yes
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Why These Are the Top Roofing Contractors in Cheshire

Cheshire's roofing market is defined by its need for durability against a challenging climate. Located in the Berkshires, the town experiences significant snowfall, freeze-thaw cycles, and occasional severe storms, leading to common issues like ice dams, wind damage, and water infiltration. Reputable local contractors are well-versed in building codes that account for snow load requirements and specialize in robust installation techniques and preventative maintenance to protect homes. The market consists of a mix of established local companies and larger regional operators serving the area.

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