The Best Roofing Contractors in Chestertown, NY

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

#1

Adirondack Roofing & Restoration

4.8
(127 reviews)
Verified

A premier full-service roofing contractor specializing in high-wind and hail damage restoration for both residential and commercial properties. They are certified by leading shingle manufacturers and are experts at navigating insurance claims. Known for their meticulous workmanship and use of premium materials designed to withstand harsh Adirondack winters.

7893 Schroon River Road, Chestertown, NY 12817

Specialties & Features

Storm Damage Restoration
Insurance Claims
Asphalt Shingles
Emergency Tarping
Roof Inspections

Business Information

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

North Country Metal Roofing Specialists

4.7
(94 reviews)
Verified

Specializes in durable, energy-efficient metal roofing systems ideal for the heavy snow loads common in Chestertown. They offer standing seam and metal shingle options with Class 4 impact resistance. Also proficient in slate and synthetic slate replacements and repairs, providing long-lasting solutions for historic and modern homes alike.

4227 Main Street, Chestertown, NY 12817

Specialties & Features

Metal Roofing
Snow Load Systems
Slate Roofing
Energy-Efficient Roofs
Commercial Roofing

Business Information

Years in Business:12 years
Licensed:Yes
Insured:Yes
#3

Chestertown Roofing & Repair

4.5
(112 reviews)
Verified

A reliable local family-owned business offering comprehensive roof repair, replacement, and maintenance services. They are highly responsive for emergency leak repairs and routine maintenance, helping to prevent small issues from becoming major problems. They work with a variety of materials and are known for their honest assessments and strong community reputation.

1010 Adirondack Avenue, Chestertown, NY 12817

Specialties & Features

Roof Repair
Preventative Maintenance
Leak Repair
Residential Re-Roofing
Tile & Shake Roofing

Business Information

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

Why These Are the Top Roofing Contractors in Chestertown

The roofing market in Chestertown, NY, is heavily influenced by its Adirondack Mountain climate, characterized by significant snowfall, freezing temperatures, and potential for severe storms. Contractors must be well-versed in constructing steep-slope roofs designed for heavy snow load shedding and using impact-resistant materials to handle hail and falling branches. Expertise in ice dam prevention, proper attic ventilation, and working with insurance companies on storm-related claims is a critical differentiator for local providers. The market is competitive among a small number of established, reputable companies.

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 Chestertown regulations and climate

Frequently Asked Questions About Roofing in Chestertown

Get answers to common questions about roofing services in Chestertown, New York.

1What is the typical cost range for a new asphalt shingle roof in Chestertown, NY, and what factors influence the price?

For a standard single-family home in Chestertown, a full asphalt shingle roof replacement typically ranges from $8,000 to $15,000. Key factors include the roof's size and pitch, the need for decking repair (common with older Adirondack homes), and the quality of shingles chosen. Local pricing is also influenced by the significant seasonal demand, with summer/fall often being more expensive due to higher contractor demand before our harsh winter sets in.

2When is the best time of year to schedule a roof replacement in the Chestertown area?

The ideal window is late spring through early fall (May to October). This avoids the heavy snowfall and freezing temperatures of our Adirondack winters, which can compromise installation quality and material flexibility. Scheduling in the shoulder seasons (spring/fall) can sometimes secure better availability, but you must be mindful of unpredictable late spring rains or early snowfalls common in Warren County.

3Are there specific roofing materials better suited for Chestertown's climate and weather?

Absolutely. Given our heavy snowfall (Chestertown averages over 80 inches annually), high wind events, and freeze-thaw cycles, impact-resistant architectural asphalt shingles (Class 3 or 4) are a popular, durable choice. Metal roofing is also an excellent long-term investment for its superior snow-shedding capabilities. It's crucial to ensure any material meets New York State building codes for wind uplift and, if applicable, local aesthetic guidelines for historic districts.

4How do I choose a reliable roofing contractor in the Chestertown/Warren County area?

Always verify that the contractor is licensed and insured in New York State and carries Workers' Compensation. Seek out local companies with a long-standing physical presence in the North Country, as they understand regional challenges. Ask for references from recent jobs in the area and check for membership in local organizations like the Adirondack Regional Chamber of Commerce, which indicates community commitment.

5My roof has ice dams every winter. Is this a major concern, and what can be done?

Yes, ice dams are a common and serious concern in Chestertown due to our climate. They indicate heat loss melting snow, which refreezes at the eaves and can cause significant water damage. The solution involves a two-part approach: improving attic insulation and ventilation to create a cold roof, and installing a waterproof ice and water shield membrane along the eaves during a roof replacement. Proper remediation is essential to prevent structural rot.