The Best Roofing Contractors in Chester, NY

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

#1

Chester Roofing & Exteriors

4.8
(142 reviews)
Verified

A full-service roofing contractor specializing in both residential and commercial projects. Known for exceptional storm damage restoration and insurance claim assistance. Uses premium materials from GAF and CertainTeed, offering strong warranty protection.

87 Brookside Avenue, Chester, NY 10918

Specialties & Features

Storm Damage Restoration
Insurance Claims
Asphalt Shingles
Emergency Services
Roof Inspections

Business Information

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

Hudson Valley Metal Roofing Specialists

4.7
(89 reviews)
Verified

Specializes in durable metal roofing systems ideal for Chester's climate, including standing seam and metal shingle roofs. Offers expertise in snow load management and ice dam prevention. Also provides asphalt and synthetic slate options with focus on energy efficiency.

212 Laroe Road, Chester, NY 10918

Specialties & Features

Metal Roofing
Snow Load Management
Energy Efficient Roofing
Commercial Roofing
Tile Roofing

Business Information

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

Orange County Storm Response Roofing

4.5
(116 reviews)
Verified

Focuses on rapid response to storm damage and emergency repairs throughout Chester and Orange County. Offers 24/7 emergency service with expertise in insurance claim documentation. Provides complete roof replacement and repair services with focus on weather-resistant installations.

55 Brookside Avenue, Chester, NY 10918

Specialties & Features

Emergency Roof Repair
Storm Damage
24/7 Service
Insurance Documentation
Roof Maintenance Programs

Business Information

Years in Business:8 years
Licensed:Yes
Insured:Yes

Why These Are the Top Roofing Contractors in Chester

Chester's roofing market is characterized by contractors experienced with the region's four-season climate, including heavy winter snow loads, ice dams, and occasional severe storms. Quality installation for weather resistance and proper ventilation are critical considerations. Most reputable contractors are well-versed in local building codes and insurance claim processes for storm damage. The market features a mix of established companies with 10+ years of service and newer specialized providers.

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

Frequently Asked Questions About Roofing in Chester

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

1What is the typical cost range for a new asphalt shingle roof replacement on a single-family home in Chester, NY?

For a standard 2,000-2,500 sq. ft. home in Chester, a full tear-off and replacement with quality architectural asphalt shingles typically ranges from $12,000 to $25,000. The final cost depends on roof complexity, the specific shingle brand/warranty chosen, and the extent of underlying decking repair needed, which is common due to our humid climate and winter snow loads. Always get 3 detailed, written estimates from local, licensed contractors for an accurate price.

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

The ideal windows are late spring (May-June) and early fall (September-October). These periods typically avoid the peak summer heat, which can make shingles too pliable during installation, and the heavy snowfall and freezing temperatures of a Chester winter. Scheduling early is crucial, as reputable local roofers' calendars fill up quickly, and unexpected spring/fall storms can cause delays.

3Are there any local building code requirements or regulations in Chester, NY, that affect roofing projects?

Yes, all roofing work in the Town of Chester requires a building permit from the local Building Department. The New York State Residential Code, which Chester follows, has specific requirements for ice and water shield installation (especially in valleys and at eaves), proper attic ventilation, and wind uplift resistance. A reputable local roofer will handle the permit process and ensure the installation meets or exceeds these codes for your protection.

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

Prioritize contractors who are licensed, insured (including Workers' Compensation and Liability), and have a verifiable physical address in the region. Ask for references from recent jobs in Orange County and check online reviews. Crucially, ensure they are a certified installer for the major shingle manufacturers (like GAF or CertainTeed), as this preserves the material warranty and indicates proper training to handle our seasonal weather extremes.

5With Chester's snowy winters and humid summers, what are the most durable roofing material options for my home?

Asphalt architectural shingles with an algae-resistant rating are the most common and cost-effective choice, performing well against moisture and snow. For longer lifespan and superior durability, consider standing seam metal roofing, which excels at shedding heavy snow and resists wind. Synthetic slate is another excellent option for a premium look with high impact resistance, which is beneficial given the potential for hail in our region.