The Best Roofing Contractors in Windsor, MA

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

#1

Windsor Peak 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 handling complex insurance claims for storm damage. They use premium materials from GAF and Owens Corning and offer strong warranties, including their own workmanship guarantee. Their team is highly experienced with New England weather challenges, including heavy snow loads and ice dam prevention.

88 Berkshire Trail, Windsor, MA 01270

Specialties & Features

Storm Damage Restoration
Insurance Claim Assistance
Ice Dam Prevention
Slate & Tile Roofing
24/7 Emergency Services

Business Information

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

Berkshire County Roofing Pros

4.6
(94 reviews)
Verified

A trusted local roofer with deep roots in the community, specializing in residential roof replacements and repairs. They excel in a wide variety of materials, including asphalt shingles, standing seam metal, and synthetic slate. Their thorough inspection process identifies potential issues from wind, hail, and winter weather, providing homeowners with durable, code-compliant solutions.

1250 Main Road, Windsor, MA 01270

Specialties & Features

Residential Roof Replacement
Metal Roof Installation
Roof Maintenance Programs
Leak Repair
Attic Ventilation

Business Information

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

Summit Commercial Roofing Systems

4.5
(68 reviews)
Verified

The leading commercial roofing expert in the Windsor area, focusing on flat and low-slope roofing systems for businesses, municipal buildings, and apartment complexes. They are certified installers for TPO, EPDM, and PVC membranes. They also provide critical commercial roof maintenance and emergency leak mitigation services to protect valuable assets from water damage.

500 Industrial Parkway, Unit 4, Windsor, MA 01270

Specialties & Features

Commercial Flat Roofing
Roof Coatings & Restoration
Emergency Leak Repair
Building Envelope Services
Preventative Maintenance Contracts

Business Information

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

Why These Are the Top Roofing Contractors in Windsor

The roofing market in Windsor, MA, is heavily influenced by its Berkshire County location, which experiences a full four-season climate with significant snowfall, ice, and occasional severe storms. This creates a high demand for durable, weather-resistant roofing systems and reliable storm damage restoration services. Local contractors must be well-versed in handling snow load calculations, preventing ice dams with proper insulation and ventilation, and navigating the insurance claim process for wind and hail damage. The market is competitive with a mix of long-established local companies and larger regional operators, with a strong emphasis on quality craftsmanship and longevity to withstand the harsh winters.

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 Windsor regulations and climate

Frequently Asked Questions About Roofing in Windsor

Get answers to common questions about roofing services in Windsor, Massachusetts.

1What is the typical cost range for a full roof replacement on a Windsor, MA home?

For a standard asphalt shingle roof on a typical single-family home in Windsor, homeowners can expect a cost range of $8,000 to $15,000, though this varies significantly with roof size, pitch, and material choice. Factors like the need for decking repair, the complexity of the roof design, and regional labor costs in Berkshire County influence the final price. We strongly recommend obtaining 2-3 detailed, written estimates from local, licensed contractors for the most accurate assessment.

2When is the best time of year to schedule a roof replacement in Windsor, given the local climate?

The ideal window for roofing in Windsor is typically late spring through early fall (May to October), avoiding the deep snows of winter and the heavy, unpredictable rains of early spring. Summer offers the most reliable dry, warm weather for proper shingle adhesion and crew safety. However, reputable local contractors are equipped to handle emergency repairs year-round and can often schedule replacements in the shoulder seasons with careful weather planning.

3Are there specific local building codes or regulations in Windsor I need to be aware of for a roofing project?

Yes, all roofing work in Windsor must comply with the Massachusetts State Building Code, which includes strict requirements for ice and water shield installation in specific zones to protect against freeze-thaw cycles common in the Berkshires. Homeowners should verify their contractor has a valid Massachusetts Construction Supervisor License (CSL) or Home Improvement Contractor (HIC) registration, and that the contractor will pull the necessary local building permit from the Windsor Building Department, which ensures code compliance and protects your investment.

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

Prioritize contractors who are locally established, licensed, insured, and can provide references from recent projects in Berkshire County. Check their standing with the Massachusetts Office of Consumer Affairs (for HIC registration) and the Better Business Bureau. A trustworthy Windsor-area roofer will offer a detailed, written contract, explain the project timeline clearly, and use high-quality materials suited to our regional climate, such as impact-resistant or algae-resistant shingles.

5What are the most common roofing problems you see on homes in Windsor due to the local weather?

The most frequent issues are ice dam damage in late winter, wind-driven rain infiltration, and damage from falling tree limbs or heavy snow loads, all exacerbated by Windsor's wooded, hilly terrain and seasonal storms. We also see accelerated wear from temperature fluctuations and moisture, which can lead to moss growth in shaded areas. Regular inspections, especially after severe weather, and proactive maintenance like gutter cleaning and tree trimming, are crucial for longevity.