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10 Best Roofers in Chesapeake, VA

More than 250 people have received a free quote in the last 60 days.

Last Updated: February 25, 2025

Maintaining the health of your roof, although important, isn't always simple. Doing regular maintenance on the roof of your Chesapeake home can help prolong its life and reduce the need for expensive repairs.

No matter the problem, there's a roofing expert in your area who can help. Use our guide of Chesapeake's top roofers to find the best one for your job.

Top 10 Best Roofers in Chesapeake

Advertisement This site receives compensation from some of the companies featured in this listing, which may impact where and how products appear. When you click "Get Quote," you will be connected with partners who may contact you with information related to your inquiry. This listing doesn't feature all companies, products, or offers that may be available.

Erie Home

Erie Home Logo

Our Rating

User Rating

7421 Central Business Park Dr #106b, Norfolk, VA 23513 (757) 937-5107 eriehome.com

Free inspections

Transparent project updates

Quality customer service

Services Offered

Replacement
Asphalt roofs
Roof repair
Metal roofs

Andrews Roofing Co Inc

Andrews Roofing Co Inc Logo

Our Rating

User Rating

757 Mt Vernon Ave, Portsmouth, VA 23707 (757) 399-3066 andrewsroofing.com

Transparent pricing

Preventive services

Free inspections

Quality customer service

Transparent project updates

Customer education

Services Offered

Replacement
Roof repair
Quality inspection
Terra cotta
Skylights
Flat roofs
Roof cleaning
Ventilation
Rubber roofs
Asphalt roofs
Slate

R.A. Woodall Roofing

R.A. Woodall Roofing Logo

Our Rating

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1115 Professional Dr Suite 5, Williamsburg, VA 23185 (757) 220-6299 rawoodallroofing.com

Free inspections

Transparent project updates

Quality customer service

Customer education

Transparent pricing

Services Offered

Wood roofs
Quality inspection
Metal roofs
Slate
Replacement
Roof repair
Rubber roofs
Flat roofs
Asphalt roofs

Streamline Roofing Williamsburg

Streamline Roofing Williamsburg Logo

Our Rating

User Rating

150 Strawberry Plains Rd STE B, Williamsburg, VA 23188 (757) 585-4362 streamlineroofingco.com

Transparent pricing

Free inspections

Quality customer service

Transparent project updates

Customer education

Preventive services

Services Offered

Metal roofs
Roof repair
Replacement
Flat roofs
Rubber roofs
Quality inspection
Ventilation

Ready Roofing Company - Williamsburg VA

Ready Roofing Company - Williamsburg VA Logo

Our Rating

User Rating

312 Lightfoot Rd Suite F, Williamsburg, VA 23188 (757) 251-9022 readyroofing.com

Locally owned

Free inspections

Quality customer service

Customer education

Transparent pricing

Reputation for timeliness

Services Offered

Metal roofs
Emergency tarp
Roof repair
Terra cotta
Replacement
Flat roofs
Ventilation
Quality inspection

The Roofing Company, Inc.

The Roofing Company, Inc. Logo

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2106 Aluminum Ave # A, Hampton, VA 23661 (757) 524-8631 theroofingcompany.com

Free inspections

Quality customer service

Preventive services

Customer education

Transparent pricing

Honors appointment windows

Transparent project updates

Services Offered

Roof repair
Slate
Skylights
Quality inspection
Replacement
Metal roofs

Burton Enterprises II Inc.

Burton Enterprises II Inc. Logo

Our Rating

User Rating

3500 Winston Ave, Virginia Beach, VA 23456 (757) 427-3344 burtonenterprisesii.com

Transparent pricing

Transparent project updates

Quality customer service

Free inspections

Services Offered

Slate
Skylights
Rubber roofs
Replacement
Ventilation
Asphalt roofs
Roof repair
Metal roofs
Mold remediation
Flat roofs
Wood roofs

Exterior Source

Exterior Source Logo

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1429 Crossways Blvd Ste B, Chesapeake, VA 23320 (757) 464-2060 exteriorsourceva.com

Free inspections

Transparent pricing

Quality customer service

Customer education

Reputation for timeliness

Preventive services

Services Offered

Replacement
Roof repair
Asphalt roofs

Chase Roofing LLC

Chase Roofing LLC Logo

Our Rating

User Rating

4504 John Tyler Hwy, Williamsburg, VA 23185 (757) 206-1948 chaseroofingva.net

Transparent pricing

Free inspections

Preventive services

Customer education

Services Offered

Quality inspection
Slate
Skylights
Flat roofs
Asphalt roofs
Wood roofs
Roof repair
Metal roofs
Replacement

Wholesale Roofers

Wholesale Roofers Logo

Our Rating

User Rating

1 Columbus Ctr #600, Virginia Beach, VA 23462 (757) 424-5981 wholesaleroofersva.com

Quality customer service

Transparent pricing

Free inspections

Preventive services

Services Offered

Flat roofs
Replacement
Roof repair
Quality inspection
Ventilation
Skylights
Asphalt roofs
Solar panel installation
Today's Homeowner Ranking Methodology

Today's Homeowner looks at dozens of datapoints on roofers to come up with our data-driven rankings. It's not possible for a company to pay for preferential treatment in our rankings. We look at the following key factors in determining who should top our list:

  • Company Experience
  • Real User Reviews
  • Company Reputation
  • Accreditations and Licenses
  • Service Area
  • Customer Service
Have questions about our methodology or company ratings? Reach out to FindAPro@TodaysHomeowner.com.

How Much Does a New Roof Cost in Chesapeake?

Price is an important consideration when replacing your roof. Below is the average price range to replace a roof on a 1,500 square foot home in Chesapeake. We also highlight prices for popular roofing materials.

How To Choose a Roofing Company

A new roof installation is a major home renovation that can cost over twenty thousand dollars total. It's crucial to research and find the most qualified and reputable roofing company for the job. Here are the top things to evaluate when hiring a roofer.

  • Experience and credentials: Companies that have been in business for over 10 years show consistent quality and customer satisfaction. Before hiring, verify that a provider has proper licenses, bonding, and insurance. Inquire about professional certifications, such as those from the National Roofing Contractors Association.
  • References and reviews: Vet companies by examining their latest customer reviews on Google, Yelp, or the Better Business Bureau (BBB) to look for a track record of consistently good feedback. You can also request recent local references to learn more about the customer experience.
  • Responsiveness and communication: From quote to project completion, your contractor should keep in consistent contact with you, answer all questions, and resolve any concerns.
  • Warranties and guarantees: A reliable roofer will provide strong guarantees from the manufacturer which protect shingles for over 30 years along with at least a 5-year workmanship warranty on labor. Be wary of shorter warranty periods.
  • Roofing materials and products: Quality roofing materials from top brands can handle Chesapeake's weather and last decades. Avoid contractors offering cheap or generic materials. Review shingle samples before deciding.
  • Detailed written estimate: Reputable roofing companies will give you a comprehensive written estimate that outlines the scope of the work, materials requirements, and total cost without hidden fees. Avoid vague quotes or ones that seem dramatically low or high.

Signs Your Roof Needs Repair or Replacement

While most homeowners don't think about their roof every day, it plays a key role in protecting your home. Watch for these common signs that your roof may be in need of professional inspection and repair.

Roof Age

The age and material of your roof are important. Asphalt shingles, the most popular residential roofing material, typically last around 20–25 years before needing to be replaced. If your roof is nearing or past this lifespan, have it evaluated to determine if full replacement is needed.

Leaks or Water Stains in Your Home

Leaks are a typical sign of roof issues. Water leaking through worn or damage shingles often leads to water stains on walls, ceilings, and insulation, or in your attic. Don't neglect even small leaks, as leaks of any size can lead to mold and other damage.

Exposed Roof Decking Underneath Shingles

If you can see roof deck boards or sheathing under shingles, it means that those shingles are severely curling or losing their seal. This means it's time for replacement. Shingles should lie flat to stop water from getting into your home.

Cracked, Broken, or Missing Shingles

Inspect your shingles closely from a sturdy ladder or while on the ground. Look for shingles that are cracked or are missing granules. Storms can cause exterior damage over time. To keep your roof in good shape, replace any missing shingles, or ones that are openly gaping.

Flashing Deterioration Around Roof Penetrations

Roof flashing provides a watertight seal around valleys, vents, chimneys, and other areas where water can penetrate your roof. Deteriorated, cracked, or peeling flashing can allow leaks. We recommend promptly resolving any problems with the roof flashing that come up.

Sagging Roof Line

A structural problem can cause your roof to display sagging or uneven slopes. If you notice sagging or an uneven slope, schedule a professional inspection. A roof deck that isn't reinforced will only get worse without proper support.

Frequently Asked Questions About Roofing in Chesapeake, VA

The best type of roofing material for your home in Chesapeake will be decided by several factors, including your budget and how often you want to do maintenance.

Asphalt is more budget-friendly, while materials like metal are more expensive but last longer. Clay roofing may be beneficial around Chesapeake due to its high solar reflectivity. Roofs of this type can help you save on cooling costs during the sunny summer months. You might be swayed by how environmentally friendly a material is, and opt for something like wood.

Roofing contractors in Virginia need to obtain a license from the Department of Professional and Occupational Regulation. The license must be classified under the roofing specialty. The license class (A, B or C) indicates the monetary value of the projects a contractor may work on.

It generally takes about one to five days to replace a roof. Factors that could influence this timeline include the accessibility of your roof, its size, and the weather in Chesapeake during the process. .

The best time of year to have your roof replaced is fall or spring. If you start your roofing job in the summer, warm weather in Chesapeake can slow down work.

The best roofing color for you is based on a few factors like the color and style of your house and the local climate. For example, if you have a Spanish style home, then you'll probably want a terracotta roof. Also, if you live in a hot climate, you may want to avoid darker colors since they absorb heat, which makes cooling your home more difficult.

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