The Best Roofing Contractors in Chester, MD

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
#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
#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

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

Frequently Asked Questions About Roofing in Chester

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

1What is the average cost to replace a roof on a typical home in Chester, MD?

For a standard asphalt shingle roof on a typical single-family home in Chester, homeowners can expect a range of $8,000 to $15,000, with the final cost heavily dependent on roof size, pitch, material choice, and the extent of any underlying decking repairs. Prices in Queen Anne's County are influenced by regional material costs and the high demand for skilled labor, especially during peak seasons. It's crucial to get multiple detailed, written estimates that break down material, labor, and waste removal costs.

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

The ideal windows are late spring (April-May) and early fall (September-October) to avoid Chester's summer heat/humidity and the potential for winter ice or nor'easters. However, urgent repairs should never be delayed. Local contractors are often busiest in late summer and fall, so scheduling several months in advance for a non-emergency replacement is wise to secure your preferred timeline and crew.

3Are there specific roofing materials or features recommended for Chester's coastal climate?

Absolutely. Given Chester's exposure to Chesapeake Bay weather—including high humidity, salt air, and strong winds—materials with high wind ratings (e.g., architectural shingles rated for 130 mph) and strong algae/moss resistance are highly recommended. Metal roofing is also an excellent, durable choice for handling heavy rain and shedding snow. Proper attic ventilation is critical to combat moisture buildup and prevent ice dams in winter.

4How do I choose a reliable roofing contractor in Queen Anne's County?

Always verify the contractor is licensed and insured in Maryland, and specifically carries workers' compensation. Ask for local references in Chester or nearby communities like Stevensville or Grasonville, and check their standing with the Better Business Bureau. A reputable local roofer will be familiar with Queen Anne's County building permit requirements and will handle the permitting process for you.

5My roof has dark streaks. Is this a major problem for homes in this area?

Those dark streaks are likely Gloeocapsa magma algae, a very common issue in Maryland's humid climate, especially in shaded areas. While not an immediate structural threat, it can degrade shingle granules over time and affect curb appeal. Professional soft washing (not high-pressure power washing) is the recommended treatment. Many modern algae-resistant shingles are available to prevent recurrence.