Top 3 Roofing Contractors in Chester

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

#1

Chesapeake Bay Roofing & Exteriors

4.8
(127 reviews)
Verified

A premier roofing contractor specializing in high-wind and storm-resistant installations for Chester's coastal climate. Experts in handling insurance claims for hail and wind damage, offering 24/7 emergency tarping and board-up services. Known for quality workmanship with GAF Master Elite certification.

201 Kent Point Road, Chester, MD 21619

Specialties & Features

Storm Damage Restoration
Insurance Claims
Emergency Services
Asphalt Shingles
Synthetic Slate

Business Information

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

Anchor Roofing Company

4.7
(94 reviews)
Verified

Family-owned roofing business with deep roots in the Chester community. Specializes in both residential and commercial roofing systems, particularly skilled with metal roofing installations that withstand coastal weather conditions. Offers comprehensive maintenance programs and thorough post-storm inspections.

1247 Main Street, Chester, MD 21619

Specialties & Features

Metal Roofing
Roof Maintenance Programs
Commercial Roofing
Tile Roofing
Roof Inspections

Business Information

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

Eastern Shore Storm Restorers

4.6
(78 reviews)
Verified

Specialized storm damage restoration experts serving the Chester area. Focus on rapid response to weather-related roofing emergencies and seamless insurance claim assistance. Certified in various roofing materials with strong expertise in wind mitigation techniques and waterproofing solutions for coastal properties.

85 Piney Narrows Road, Chester, MD 21619

Specialties & Features

Emergency Storm Response
Insurance Claim Assistance
Wind Damage Repair
Waterproofing
Roof Replacement

Business Information

Years in Business:12 years
Licensed:Yes
Insured:Yes
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Why These Are the Top Roofing Contractors in Chester

Chester's roofing market is heavily influenced by its Chesapeake Bay coastal location, requiring specialized expertise in wind-resistant installations and storm damage repair. The area experiences nor'easters, tropical systems, and occasional hail, making quality roofing materials and proper installation critical. Local contractors must be well-versed in Maryland building codes and coastal construction standards. The market features a mix of established local companies and regional providers, with an emphasis on storm resilience and insurance claim expertise.

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