Updated June 2026

Top 10 Roofing Contractors in Chesapeake

Vetted, licensed roofing contractors serving Chesapeake and the Hampton Roads region of coastal Virginia.

Quick Comparison

Rank Company Specialty Experience BBB Website
1 Exterior Source Best Overall Since 1993 A+ Accredited Visit
2 Atlantic Craftsman LLC Most Established Since 1974 Visit
3 Premier Roofing & Siding Contractors, Inc. Best for Owens Corning Systems Since 1989 A+ Accredited Visit
4 Clark Roofing & Siding, Inc. Best for New Construction Since 1997 A+ Accredited Visit
5 WT Anderson Roofing & Siding Best for Storm & Insurance Claims Local A+ Rating Visit
6 Gilpin Roofing Best for Residential Replacement 30+ Yrs A+ Rating Visit
7 Roof Pros of Virginia, LLC Best for Warranty Coverage 25+ Yrs A+ Accredited Visit
8 Roofing Systems of Hampton Roads Best for Specialty & Luxury Roofs Since 2005 A+ Accredited Visit
9 United Roofing Corporation Best for Commercial & Flat Roofs Since 2012 Listed Visit
10 Gray Line Roofing Best Veteran-Owned Roofer 10+ Yrs Visit

Detailed Reviews

#2

Atlantic Craftsman LLC

Most Established
ExperienceSince 1974 (50+ Years)
BBB Status
SpecialtyResidential & Commercial Roofing
Service AreaChesapeake & Hampton Roads

Founded in 1974, Atlantic Craftsman has been roofing Hampton Roads homes for over 50 years and now operates as a third-generation, family- and veteran-owned business headquartered in Chesapeake. It is a GAF Master Elite contractor offering tiered GAF warranties including the Golden Pledge. Services span roof replacement and repair, commercial flat roofing, siding, windows, doors, gutters and skylights.

Roof Replacement Roof Repair Storm Restoration Commercial Flat Roofing Siding Gutters Skylights
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#3

Premier Roofing & Siding Contractors, Inc.

Best for Owens Corning Systems
ExperienceSince 1989 (36+ Years)
BBB StatusA+ Accredited
SpecialtyResidential Roofing & Siding
Service AreaChesapeake & Hampton Roads

Operating since 1989, Premier Roofing & Siding is a locally owned, family-operated and woman-led contractor that has been BBB Accredited with an A+ rating since 1991. It is an Owens Corning Platinum Preferred Contractor and a CertainTeed certified siding installer. Premier installs asphalt shingle, flat and TPO roofs and handles siding, gutters, windows, skylights and storm-damage repairs.

Roof Replacement Roof Repair Flat & TPO Roofing Siding Gutters Windows Storm Damage
Visit Premier Roofing & Siding Contractors, Inc.
#4

Clark Roofing & Siding, Inc.

Best for New Construction
ExperienceSince 1997 (27+ Years)
BBB StatusA+ Accredited
SpecialtyResidential & Commercial Roofing
Service AreaChesapeake & Hampton Roads

Founded in Chesapeake in 1997 by Chuck Clark, Clark Roofing & Siding is a Class A contractor that has been BBB Accredited with an A+ rating since 2007. Through long-standing builder relationships it installs roofs and siding on new-construction homes across Hampton Roads and northeastern North Carolina. The company offers residential and commercial roofing plus in-house metal roofing and fabrication.

Roof Replacement Roof Repair Metal Roofing & Fabrication Commercial Roofing Siding New Construction Roofing Property Management
Visit Clark Roofing & Siding, Inc.
#5

WT Anderson Roofing & Siding

Best for Storm & Insurance Claims
ExperienceEstablished local roofer
BBB StatusA+ Rating
SpecialtyResidential & Commercial Roofing
Service AreaChesapeake & Hampton Roads

WT Anderson is a GAF Master Elite contractor and 2025 GAF President's Club member, a recognition reserved for the top tier of GAF-certified roofers. The company holds a Virginia Class A contractor license (#2705137326) and an A+ BBB rating. It handles roof repair, replacement and inspections, commercial TPO/EPDM/PVC systems, siding, gutters and windows, and offers financing and quote requests for storm and insurance work.

Roof Replacement Roof Repair Roof Inspection Commercial TPO/EPDM Roofing Siding Gutters Windows
Visit WT Anderson Roofing & Siding
#6

Gilpin Roofing

Best for Residential Replacement
Experience30+ Years
BBB StatusA+ Rating
SpecialtyResidential Roofing
Service AreaChesapeake & Southside Hampton Roads

Gilpin Roofing has been a Hampton Roads roofer for more than 30 years and is a GAF Master Elite contractor that has earned the GAF Presidential Award. Locally owned and operated, it reports serving more than 5,000 homes and carries an A+ BBB rating. Services include roof replacement and repair, skylights and flashing, flat and commercial roofing, multi-family installations and roof certifications.

Roof Replacement Roof Repair Skylights & Flashing Flat Roofing Multi-Family Roofing Roof Certifications
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#7

Roof Pros of Virginia, LLC

Best for Warranty Coverage
Experience25+ Years Experience
BBB StatusA+ Accredited
SpecialtyResidential & Commercial Roofing
Service AreaChesapeake & Hampton Roads

Based on North Battlefield Boulevard in Chesapeake, Roof Pros of Virginia is a family-owned GAF Master Elite contractor that emphasizes the GAF Golden Pledge warranty and upfront pricing. The company is BBB Accredited with an A+ rating (accredited since 2021) and cites over 25 years of hands-on experience. It offers residential and commercial roofing, metal and fortified roofing, siding, gutters and windows.

Roof Replacement Roof Repair Metal Roofing Fortified Roofing Commercial Roofing Siding Gutters
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#8

Roofing Systems of Hampton Roads

Best for Specialty & Luxury Roofs
ExperienceSince 2005 (19+ Years)
BBB StatusA+ Accredited
SpecialtyResidential Roofing
Service AreaChesapeake & Hampton Roads

A family-owned Chesapeake company operating since 2005, Roofing Systems of Hampton Roads is BBB Accredited with an A+ rating (accredited since 2012). It is trained to install a wide range of systems including asphalt shingles, flat/membrane, metal, specialty and luxury shingles, plus slate and synthetic slate. It also offers emergency tarp-ups, window and door replacement, skylights and seamless gutters.

Roof Replacement Roof Repair Slate & Synthetic Slate Metal Roofing Flat/Membrane Roofing Seamless Gutters Emergency Tarp-Up
Visit Roofing Systems of Hampton Roads
#9

United Roofing Corporation

Best for Commercial & Flat Roofs
ExperienceSince 2012 (12+ Years)
BBB StatusListed
SpecialtyCommercial & Residential Roofing
Service AreaHampton Roads & Chesapeake

Serving the Hampton Roads region since 2012, United Roofing Corporation is a locally and family-owned contractor that is an Owens Corning Platinum-certified roofer and authorized GAF contractor. It focuses heavily on commercial roofing and flat-roof systems, including roof coatings, alongside residential installation, repair, gutters, skylights and storm-damage and insurance-claim work.

Commercial Roofing Flat Roofing Roof Coatings Roof Replacement Roof Repair Gutters Storm Damage Repair
Visit United Roofing Corporation
#10

Gray Line Roofing

Best Veteran-Owned Roofer
Experience10+ Years
BBB Status
SpecialtyResidential & Commercial Roofing
Service AreaChesapeake & Hampton Roads

Headquartered in Chesapeake, Gray Line Roofing is a Veteran-, Professional Engineer- and Class A contractor-owned company that has served residential and commercial clients across the region for over ten years. It specializes in flat roofing, asphalt shingle roofing and commercial solutions, and provides roof inspections, virtual estimates, insurance-claim assistance, financing and veteran discounts.

Roof Replacement Roof Repair Flat Roofing Asphalt Shingle Roofing Commercial Roofing Roof Inspections Insurance Claims
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How to Choose a Roofing Contractor in Chesapeake

Verify a Virginia DPOR contractor license

Any roofing job in Chesapeake exceeding $1,000 in labor and materials must be performed by a contractor licensed by the Virginia Department of Professional and Occupational Regulation (DPOR). For a full roof replacement, look for a Class A license (no dollar cap); Class B caps projects at $149,999 and Class C at $29,999. Ask for the firm's license number and confirm its class and status on the DPOR website before signing.

Confirm they pull a City of Chesapeake permit

Chesapeake requires a building permit for roof replacement, even when you are simply re-covering with the same material. A reputable local roofer handles the permit through the City of Chesapeake Development and Permits Department as part of the contract (the permit itself runs around $157). Be wary of any contractor who suggests skipping the permit to save money.

Insist on manufacturer certification for the warranty

Coastal Virginia's wind and humidity make warranty coverage important. GAF Master Elite contractors (only about 2% nationwide) can register the Golden Pledge warranty, and Owens Corning Platinum Preferred contractors can offer extended coverage. These manufacturer programs are only honored when a certified installer does the work, so verify the certification before relying on the warranty.

Choose wind- and hurricane-rated systems

Chesapeake sits in a hurricane-exposed coastal zone, so ask how the contractor meets local wind requirements: enhanced nailing patterns, sealed underlayment, starter strips and ridge caps, and shingles rated for high winds. Contractors who routinely work Hampton Roads insurance claims understand the documentation needed when storm damage occurs.

Check proof of insurance and local longevity

Virginia contractors should carry general liability and, if they have employees, workers' compensation. Ask for current certificates. Favor companies with a verifiable track record in Hampton Roads, several of the firms on this list have served Chesapeake for two to five decades, which means they will likely be around to honor a workmanship warranty.

Get multiple written estimates and check BBB standing

Roof replacement in Chesapeake commonly runs into the tens of thousands of dollars, so collect at least two or three itemized written estimates that spell out materials, underlayment, flashing, tear-off and cleanup. Cross-check each company on the Better Business Bureau of Greater Hampton Roads, where several area roofers hold A+ accreditation, and read recent reviews.

Frequently Asked Questions

For a typical Chesapeake home, asphalt shingle roof replacement generally falls in the range of about $9,000 to $15,000, with larger or more complex roofs running higher. Local cost guides put pricing around $330 to $550 per roofing square (100 sq ft), and premium materials like metal cost considerably more. Get itemized quotes, since roof size, pitch, tear-off and material choice all move the price.
Architectural asphalt shingles rated for high wind are the most common and cost-effective choice locally. For better longevity in the salt air, humidity and storm exposure of Hampton Roads, standing-seam metal and synthetic slate are popular upgrades. Flat and low-slope buildings typically use TPO, EPDM or membrane systems. Whatever you pick, proper sealed underlayment and wind-rated installation matter more here than in inland areas.
Yes on both counts. The City of Chesapeake requires a building permit for roof replacement (about $157), and Virginia law requires a DPOR-licensed contractor for any roofing work over $1,000. A full replacement should be done by a Class A licensed firm. A good local roofer pulls the permit for you and works to the Virginia Uniform Statewide Building Code.
In Chesapeake's humid, storm-prone coastal climate, a quality architectural asphalt shingle roof typically lasts about 20 to 30 years, somewhat less than in milder inland regions because of UV exposure, wind and moisture. Metal and slate-style roofs can last 40 years or more. Routine inspections after major storms and keeping gutters clear help you reach the upper end of that range.
Look for a verifiable Virginia Class A DPOR license, current liability insurance, and a willingness to pull the City of Chesapeake permit. Manufacturer certifications such as GAF Master Elite or Owens Corning Platinum unlock stronger warranties. Prioritize companies with a long, documented track record in Hampton Roads and solid BBB standing, and always get a detailed written estimate before work begins.
Chesapeake faces hot, humid summers, frequent thunderstorms, occasional tropical storms and hurricanes off the Atlantic, plus salt-laden coastal air. These conditions accelerate shingle aging, drive wind uplift and create persistent moisture that can feed algae, moss and rot. That is why wind-rated shingles, proper attic ventilation, quality flashing and sealed underlayment, and prompt storm inspections are especially important for local homes.

Roofing in Chesapeake

Chesapeake sits in southeastern Virginia's Hampton Roads region, where roofs face a demanding mix of coastal weather. Summers are hot and humid with frequent, sometimes severe thunderstorms, and the city's location near the Atlantic and Chesapeake Bay exposes it to tropical storms and hurricanes that bring damaging wind and wind-driven rain. Salt air, high humidity and intense UV all accelerate the aging of roofing materials, while low-lying, flood-prone terrain raises the stakes on keeping water out. These drivers make wind resistance, moisture management and storm readiness the central concerns for any Chesapeake roof.

The dominant roofing material across Chesapeake's neighborhoods is the architectural asphalt shingle, valued for its balance of cost, durability and wind ratings suited to coastal conditions. Homeowners looking for longer life increasingly choose standing-seam metal or synthetic slate, both of which stand up well to salt air and storms, while traditional and synthetic slate appear on higher-end and historic homes. Chesapeake's many flat and low-slope residential additions and its commercial and industrial buildings rely on membrane systems such as TPO, EPDM and PVC. Seamless gutters and proper attic ventilation are common companions to any new roof here.

Roofing work in Chesapeake is regulated at both the state and city level. Virginia requires any contractor performing roofing work valued over $1,000 to hold a license from the Department of Professional and Occupational Regulation (DPOR), issued in three classes: Class A (no project limit), Class B (up to $149,999) and Class C (up to $29,999), with a roofing specialty designation. The City of Chesapeake separately requires a building permit for roof replacement, typically costing around $157, and work must comply with the Virginia Uniform Statewide Building Code. A licensed local contractor normally pulls the permit and schedules inspections as part of the job.

Because Chesapeake's coastal exposure punishes shortcuts, choosing an experienced, properly licensed local contractor matters more here than in many markets. A roofer who works Hampton Roads year-round understands the wind-uplift requirements, the salt-and-humidity wear patterns, and the insurance-claim process that follows a tropical storm. Manufacturer certifications like GAF Master Elite and Owens Corning Platinum Preferred unlock the strongest warranties, but only when a certified installer does the work. Several established Chesapeake firms, some with three to five decades in business, combine that certification, a verifiable Class A license and BBB accreditation, giving homeowners confidence the company will still be there to back its workmanship.

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