Best Roofing Companies Near You in Chesapeake, VA (2026)

58 Verified Contractors 4.9 Avg Rating 10,452 Total Reviews AI-Analyzed Reviews Free Estimates Available

Top Roofers in Chesapeake, VA

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Roof Artistry

5(65 reviews)
Based in ChesapeakeOnline EstimatesVeteran-Owned
AI Review Summary

Roof Artistry, led by Paul, earns consistent praise for thorough roof inspections, clear communication, and honest recommendations tailored to each customer's needs and budget. Customers appreciate the team's professionalism, timely service, meticulous cleanup, and follow-up care, with Paul taking time to explain issues in understandable terms and provide detailed photo documentation. The company's expertise with complex roofing projects—including slate roofs and specialty repairs—combined with competitive pricing and respectful craftsmanship, makes them a trusted choice for homeowners seeking reliable roofing solutions.

"I have an old slate roof on my over 100 year old house which has been in my family since the mid 1960s. I had a large well known slate roofing company over the years repair this old slate roof but it always kept leaking. This companies would fly drones over the roof and then explain based on the drone coverage that I had broken slate that needed to be replaced. I eventually asked for a water test to accurately identify leaks before getting…" — jeanette j.
1226 Executive Blvd Ste 101
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmedWarranty - Not confirmed

+1 757-955-0107

Jayhawk Exteriors

4.9(332 reviews)
Based in Chesapeake24/7 EmergencyOnline EstimatesVeteran-Owned
AI Review Summary

Jayhawk Exteriors earns consistent praise from customers for their expert knowledge, high-quality materials (including GAF master elite products), and meticulous workmanship that goes beyond standard expectations. Customers particularly appreciate the company's responsive communication, transparent explanations of work, timely scheduling, and thorough cleanup—with owner Nick earning recognition for keeping homeowners informed and at ease throughout the process. The combination of fair pricing, comprehensive warranties, and attention to detail—whether replacing full roofs, addressing emergency leaks, or repairing interior damage—has resulted in strong referrals and repeat business, including from customers in the property insurance industry.

"Fantastic company. I cannot say enough good things about this company, recently I had a pretty bad roof leak, which also caused damages to the interior of my home. Jayhawk Exteriors was able to not only fix the roof, but they also determine that it was coming from the skylight!! They fixed my skylight also so it would not continue to be a problem. Nick kept me updated on the entire process and made me feel at ease about the timeline. They also…" — Lauren L.
1824 Engle Ave
Licensed - Not confirmedInsured - Not confirmed✓ 23 yrs in business✓ Warranty Offered

+1 757-963-6559

Gray Line Roofing

4.9(145 reviews)
Based in ChesapeakeOpen WeekendsSpanish SpeakingVeteran-OwnedWomen-Owned
AI Review Summary

Gray Line Roofing earns consistent praise for exceptional professionalism, quality craftsmanship, and thorough communication throughout every project phase. Customers particularly appreciate the team's efficiency—completing jobs quickly while maintaining meticulous cleanup and attention to detail—as well as transparent pricing and personalized service from initial assessment to final inspection. The company's commitment to customer satisfaction is evident in their responsiveness, skilled workmanship, and respectful treatment of both homes and families.

"Quite simply, The Best! We could not be happier with our results from start to finish. From Rob, who was canvassing our neighborhood, to Roger who explained everything in terms we could understand, to Tyler who managed the actual install, this team is quite simply the best. Rob was incredibly respectful when he stopped by our house. Roger was thorough and answered all of our questions and addressed our concerns upfront. Tyler was kind and…" — Angela M.
713 Fenway Ave Suite 3
✓ LicensedInsured - Not confirmed✓ 10 yrs in businessWarranty - Not confirmed

+1 757-263-0232

Exterior Source of Tidewater, VA

4.8(289 reviews)
Based in ChesapeakeOpen WeekendsSpanish Speaking
AI Review Summary

Exterior Source consistently earns praise for exceptional craftsmanship, attention to detail, and professionalism across all stages of projects—from initial consultation through installation and follow-up. Customers particularly value the company's clear communication and transparency, with team members keeping homeowners informed throughout the process and ensuring quality work is completed as promised. The company's knowledgeable staff and pride in their work have made customers eager to recommend them and return for future projects.

"I’d been going back and forth on getting my vinyl siding and gutters redone on my house for quite some time now. After reaching out to a couple different companies I ended up going with Exterior Source. From speaking with the sales consultant Jason he explained everything about their product and the whole process of how the job would go. To the project lead/manager Nick keeping me aware of the job progress and little adjustment they had to make…" — Brnfrd J.
1429 Crossways Blvd Ste B
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmedWarranty - Not confirmed

+1 757-464-2060

Clark Roofing & Siding Inc

4.8(140 reviews)
Based in Chesapeake24/7 EmergencyOpen Weekends
AI Review Summary

Clark Roofing and Siding consistently earns praise for their professionalism, efficiency, and expert craftsmanship, with customers highlighting their punctuality, clean work practices, and ability to complete projects in minimal time. The company stands out for exceptional customer communication and personalized service, with owner Chuck demonstrating deep product knowledge—particularly in custom metal roof design and installation—and taking time to address customer concerns and even identify hidden damage. Customers also appreciate their comprehensive in-house services, including on-site gutter fabrication and installation, along with their commitment to delivering quality results that exceed expectations.

"I would recommend Clark’s Roofing to everyone! They were on point starting with coming out for the estimate. Even saved us money by pointing out damage from a hail storm that came through. We didn’t realize just how much damage was there, we had just purchased the home 3 years ago and was so thankful for his expertise and knowledge. The crew was so efficient, respectful and professional. Clean up was amazing! Our new roof and gutters really…" — Heather H.
1755 W Rd
✓ LicensedInsured - Not confirmed✓ 29 yrs in businessWarranty - Not confirmed

+1 757-485-1000

Roof Pros of Virginia

4.8(72 reviews)
Based in Chesapeake
AI Review Summary

Roof Pros of Virginia consistently delivers professional service and high-quality craftsmanship, with customers praising the owner Dave and his crew for their efficiency, thorough communication, and meticulous cleanup on every project. The company stands out for transparent pricing, top-quality materials with warranties, and a straightforward estimate process without high-pressure sales tactics. Customers appreciate the team's punctuality, politeness, and commitment to keeping them informed throughout the project while maintaining competitive pricing that often beats other quotes.

"Great company. Owner is professional, friendly and a great person. Not pushy about just getting the job. Gives you a estimate and tells you up front what the job entails, and let's you get back to him when your ready. Your phone and text is not getting blown up daily. Top quality materials, and workmanship. The crew was on time, professional, hard working, polite, and cleaned up the site well. Communication on project was excellent. Pricing and…" — Reginald T.
445 Battlefield Blvd N E
Licensed - Not confirmedInsured - Not confirmed✓ 30 yrs in businessWarranty - Not confirmed

+1 757-277-9100

Best Choice Roofing

4.7(286 reviews)
Based in ChesapeakeOnline Estimates
AI Review Summary

Best Choice Roofing earns consistent praise for their knowledgeable and personable consultants—particularly Alex and Kaleb—who provide thorough inspections, honest assessments, and patient guidance through both the sales process and insurance claims. Customers appreciate the professionalism and quality workmanship of the installation crews, efficient timelines, and the peace of mind offered by their lifetime warranty on labor and materials. The company stands out for going above and beyond, from climbing high roofs for inspections that competitors skip to actively managing insurance claims and offering multiple discount options to maximize customer value.

"Outstanding! From the very start when we first met with Alex, we already felt comfortable discussing with him our requirements. He went above and beyond by climbing up to our high roof to inspect and check the condition of our roof. He took plenty of pictures and even collected loose nails. Other vendors that we invited did not bother going up for the free inspection. Alex discussed with us the company's history and he showed us the products BCR…" — Wilfredo R.
2010 Old Greenbrier Rd Suite N
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmedWarranty - Not confirmed

+1 757-913-5029

Premier Roofing & Siding Contractors

4.7(206 reviews)
Based in ChesapeakeOnline EstimatesWomen-Owned
AI Review Summary

Premier Roofing & Siding consistently earns praise from customers for their professionalism, quality craftsmanship, and exceptional communication throughout every stage of projects. Clients repeatedly highlight competitive pricing, prompt scheduling, thorough cleanup, and a willingness to handle unexpected issues transparently and efficiently. The team's reliability—completing multiple projects quickly while maintaining high standards—makes them a trusted choice for roofing, siding, gutters, and related home improvements.

"By far this was the best company to use for our gutter repair. Great service over phone and in person. They gave us the best quote. Came out in less than a week and did amazing work repairing our gutter, facia and soffit. I added something that I needed to be fixed in different location from oriiginal repair and they repaired that too. First 2 pictures where orginal problem. Lasf 2 pitures are repair and final product. Got multiple quotes and…" — Lisa 2.
1215 Bainbridge Blvd
Licensed - Not confirmedInsured - Not confirmed✓ 37 yrs in business✓ Warranty Offered

+1 757-335-6950

Patriot Exterior Solutions

4.7(131 reviews)
Based in ChesapeakeVeteran-Owned
AI Review Summary

Patriot Exterior Solutions, led by owner Omar, consistently delivers exceptional craftsmanship and outstanding customer service, with clients praising the quality of their roof replacements and exterior work. Customers particularly appreciate Omar's responsiveness and quick turnaround times—often completing estimates and installations within days—as well as his competitive pricing that undercuts competitors by significant margins. The crew is noted for their professionalism, diligence, thorough cleanup, and attentiveness to customer concerns, making them a trusted choice for homeowners seeking reliable exterior solutions.

"I recently had my roof replaced by Patriot Exterior and I couldn’t be happier. Omar showed me several quality samples, was quick to give me an estimate, and then schedule the installation. His crew were unbelievable - they worked tirelessly for three days, were helpful when I needed to let my dogs out for breaks, and then left the area spotless when the roof was completed. This new roof makes the house really stand out and once I get the shutters…" — Martha E.
553 Graphite Trl
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmedWarranty - Not confirmed

+1 757-426-5200

M&A Exterior Home Improvement

4.7(81 reviews)
Based in ChesapeakeOnline EstimatesSpanish Speaking
AI Review Summary

M&A Exterior consistently delivers professional, high-quality work with excellent communication and competitive pricing. Customers praise their efficient project completion, meticulous attention to detail, and friendly, courteous team members who keep homeowners informed throughout the process. The company's owner is highly responsive, and clients frequently return for repeat work, citing reliable workmanship and fair pricing as key reasons for their loyalty and strong recommendations.

"Absolutely fabulous to work with! We had an amazing experience from the day we received our quote until the completion of the project. Everyone in our neighborhood who encountered any of the team shared that they were so friendly, and we agree! They kept us informed every step of the way and were so efficient and hardworking. I would 100% recommend working with this company for anything you need done! Our house doesn’t look anything like it did…" — Kara H.
3609 S Battlefield Blvd
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed✓ Warranty Offered

+1 757-779-5244

Chesapeake Roofers at a Glance

Of the 58 roofing companies serving Chesapeake:

10
Based in Chesapeake
16
List a license
13
List insurance
21
24/7 emergency service
38
Open weekends
22
Offer online estimates
7
Spanish-speaking staff

Based on what each company lists on its profile or website. Always confirm licensing and insurance directly.

FAQ: Roofers in Chesapeake, VA

58 roofing companies serve Chesapeake in our directory, with an average Google rating of 4.9 across 10,452 reviews. 16 list a license and 13 list insurance — ask any contractor for proof of both before work begins.