Best Roof Repair in Chesapeake, VA — Top Roofers (2026)

20 Verified Contractors 5.0 Avg Rating 5,102 Total Reviews AI-Analyzed Reviews

Top Roofers in Chesapeake, VA

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ACE Home Improvements

5(300 reviews)
Online EstimatesOpen WeekendsVeteran-OwnedMinority-Owned
AI Review Summary

ACE Home Improvements earns consistent praise for responsive communication, competitive pricing, and swift project execution. Customers particularly value the team's attention to detail and commitment to understanding their vision, with crew members like Marc and Rob taking time to refine plans and provide helpful suggestions. The company's reliability and efficient workmanship have made customers confident in recommending ACE for future home improvement needs.

"The assigned contractors were second to none. They executed exactly as promised and completed tasking on time. Exceeded expectation. I would suggest offering a standard contract agreement for services provided vice an email. Virtual business is good but in my business I find it helpful to ensure face to face meeting for that personal touch. The time is soon coming when machines replace humans but that time is not now. The folks that i did…" — Charles M.
5629 Normandy Ave
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-424-7283

Matrix Construction of Hampton Roads, Inc.

5(165 reviews)
24/7 EmergencyOpen Weekends
AI Review Summary

Matrix Construction, led by owner Nelson Pena, earns consistent praise for exceptional professionalism, responsive communication, and fair pricing. Customers highlight the team's thorough explanations, prompt service, efficient work, and commitment to standing behind their results with quality materials. The crew's courteous demeanor, reliability in all weather conditions, and attention to detail—including leaving work areas clean—make them a trusted choice for roofing and exterior home projects.

"Nelson is beyond fantastic, I can not say enough good things! The original contractor I had over to look at my siding, gutter, and roof gave me the most insane estimate. When I contacted Nelson he made sure to come by quickly, and then walked me through everything going on and what all of the options were. The pricing was beyond fair, he did fantastic work, and he was honest and responsive. I can not say enough good things about him and his…" — John B.
1443 Picadilly St
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-641-0738

Prime Time Pressure Washing & Roof Cleaning

5(164 reviews)
Online EstimatesOpen Weekends
AI Review Summary

This roofing and exterior cleaning company is praised by customers for its professionalism, responsiveness, and thorough attention to detail across all services. Pat and his crew consistently deliver high-quality work—from roof cleaning and soft washing to seasonal installations—while remaining flexible with scheduling and budget concerns, as demonstrated by before-and-after documentation of their results. Customers particularly appreciate the company's courteous communication and timely service, with multiple reviews highlighting how their work restores homes to like-new condition.

"We moved into our new house less than a year ago but because of the location by the Currituck sound, our house looked pitiful from the midges. We couldn't even begin to clean it ourselves. We contacted Pat and he was very thorough with explaining the process and worked with us on scheduling and promptly came out to give us an in person estimate. His work was cut out for him with out white board and batten siding. After the work was complete our…" — Kim A.
115 White Oak Dr
Licensed - Not confirmed✓ InsuredYears - Not confirmed

+1 252-582-7873

Handyman Haulers

5(106 reviews)
Open Weekends
AI Review Summary

Handyman Haulers earns consistent praise for exceptional professionalism, responsiveness, and reliable execution across demolition and cleanout projects. Customers highlight owner Andy's strong communication—including rapid response times even outside business hours—and his team's ability to complete jobs on schedule and as promised. The company is recognized for fair pricing, thorough work, and the skill to handle complex projects seamlessly, making customers feel confident and stress-free throughout the process.

"Handyman Haulers did an outstanding job clearing out a family home on a very short timeline at a fair price. Andy was eager to earn my business and was a very strong communicator throughout the entire process. He had necessary equipment for a full house cleanout and completed the job as discussed without any issues whatsoever. I was impressed with the professionalism, skill and thoroughness and would highly recommend Handyman Haulers for…" — Courtney P.
Mohawk Rd
Licensed - Not confirmed✓ InsuredYears - Not confirmed

+1 912-722-9871

Wholesale Roofers

5(96 reviews)
24/7 EmergencyOnline EstimatesOpen Weekends
AI Review Summary

Wholesale Roofers earns consistent praise for exceptional craftsmanship, premium GAF materials backed by limited lifetime warranties, and professionalism throughout every project stage. Customers highlight responsive communication, on-time and on-budget completion, thorough cleanup, and a dedicated team that prioritizes getting the job done right the first time. The company stands out for honest assessments and transparent recommendations, offering customers confidence that they're investing in quality work and materials designed to last decades.

"For me, this was a absolutely great choice. I was on the edge whether I wanted to purchase a roof and pay this much money for it. I am glad I chose Wholesale roofers. The selling point is the GAF materials, the limited lifetime warranty and the Wholesale roofers amazing team. The amount of care they put in to doing this job right the first time is outstanding. This roof should last up to 5 decades. The GAF company will end up mailing me my…" — Mission I.
732 Thimble Shoals Blvd Ste. 302A-900
Licensed - Not confirmedInsured - Not confirmed✓ 13 yrs in business

+1 757-271-3803

Domi Roofing

5(94 reviews)
24/7 EmergencyOnline EstimatesOpen Weekends
AI Review Summary

Domi Roofing consistently earns praise for exceptional professionalism, quality craftsmanship, and transparent communication throughout the entire project. Customers appreciate owner Vasili's personalized approach, competitive pricing paired with premium materials, and the crew's efficiency—completing jobs quickly while maintaining meticulous attention to detail and leaving properties clean. The company's commitment to delivering exactly what they promise, combined with honest sales practices and strong follow-through, has made them a highly recommended choice for homeowners seeking reliable roofing services.

"I'm a retired owner of a hardware store that dealt with contractors all the time...I know what to look for in quality....well ..the bar was just raised with Domi roofing!!!! These guys do exactly what they say they will do and more...I inspected every detail of the riof when they left before they came back the next day...well... I just smiled. ..finally got what I paid for and more!!! First check I wrote in a long time where I…" — John R.
2589 Quality Ct # 303
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-737-9286

Knight Exteriors LLC

5(86 reviews)
24/7 EmergencyOpen Weekends
AI Review Summary

Knight Exteriors earns consistent praise for exceptional craftsmanship and meticulous attention to detail on both roofing and deck projects, with customers highlighting the quality and durability of finished work. Clients consistently commend the team's professionalism and responsiveness, particularly owner Eric's involvement in projects from initial estimate through completion, along with proactive communication that keeps homeowners informed throughout the process. The company also stands out for reliable project management—showing up on time, completing work efficiently, and leaving job sites thoroughly cleaned—while maintaining competitive pricing and a strong work ethic that prioritizes getting the job done right.

"We couldn’t be happier with our new deck from Knight Exteriors. The quality of the build is outstanding — everything feels solid, thoughtfully designed, and beautifully finished. Their attention to detail really shows, from the clean lines and trim work to the overall craftsmanship. Communication throughout the process was also excellent; they kept us informed and answered questions promptly, which made the whole experience feel smooth and…" — Bente W.
Grace St
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-751-3831

Armor Roofing

5(73 reviews)
24/7 EmergencyOpen Weekends
AI Review Summary

Armor Roofing is a family-owned company praised by customers for exceptional quality workmanship, competitive pricing, and outstanding customer service. Homeowners consistently highlight owner Ricky Comer's honesty, reliability, and commitment to excellence—including his willingness to redo work to meet his own high standards and complete projects efficiently. The team's professionalism extends to thoughtful job site practices, detailed communication, and going above and beyond promises, making them a trusted choice for roof replacements and gutter installations in the Yorktown area.

"I had my 19 year old roof replaced by Mr. Ricky Comer's Armor Roofing Company located at 4111 George Washington Memorial Hwy, Yorktown VA 23692. His roofing crew removed the plants and flower pots off of my deck and covered all of my shrubs before they removed the old roof shingles from my house and my shed. They replaced bad plywood panels with new plywood and they practically sealed my roofs with synthetic overlayment and ice and water shield.…" — Lester J.
4111 George Washington Memorial Hwy
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-765-2241

Roof Artistry

5(65 reviews)
Online 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 confirmed

+1 757-955-0107

Pristine Exteriors | WASH 757

5(65 reviews)
Online EstimatesOpen WeekendsVeteran-Owned
AI Review Summary

This roofing company is known for exceptional professionalism, reliability, and genuine care for customers—whether taking on jobs or going out of their way to refer clients elsewhere. Technicians demonstrate meticulous attention to detail, arriving on time and communicating throughout the process to ensure thorough, high-quality work that consistently exceeds expectations. Customers particularly appreciate the personable demeanor and integrity of the team, with many noting they wouldn't hesitate to book again.

"The first thing I look for in service is the demeanor and appearance of the technician. I could tell right up front that Jay was going to do a great job. Great handshake, great smile, great energy, willing conversation, they all met A++ points on my checklist. Additionally, I appreciate the snapshot he shared of who he is and the highlights of his life, especially his service in the U. S. Marine Corps. As a veteran myself, our conversation was…" — Ken
102 Chippenham Dr
Licensed - Not confirmed✓ InsuredYears - Not confirmed

+1 757-303-9021

DNG Construction LLC

5(63 reviews)
Online EstimatesOpen WeekendsSpanish SpeakingMinority-Owned
AI Review Summary

DNG Construction consistently earns praise for their exceptional craftsmanship and attention to detail, with customers highlighting the quality of their siding and exterior work that transforms homes. Clients appreciate their professionalism, punctuality, and efficiency—team members arrive on time or early, work diligently, and complete projects in a timely manner while maintaining a clean work site. The company is also recognized for providing competitive pricing and responsive service, with owner Jose offering prompt estimates and fair quotes that customers find better than competitors.

"Jose and Santos are AWESOME !!! They put siding on our old 1950’s house . They were on time everyday. Even early each day ! They did an OUTSTANDING job . So professional and very hard workers ! Our home looks absolutely beautiful. Neighbors were stopping by to say what a fantastic Job they did on the siding ! I would hire them again! I have given their name to some People and I will continue to do that as they are OUTSTANDING ! Cleaned…" — Helen M.
335 Rogers Ave
✓ LicensedInsured - Not confirmed✓ 18 yrs in business

+1 757-581-5519

Metal Roofing Virginia Beach

5(52 reviews)
Open Weekends
AI Review Summary

This roofing company consistently delivers exceptional results through meticulous attention to detail, punctual project completion, and clear communication with homeowners throughout the process. Customers praise the team's professionalism, skilled workmanship, and thorough cleanup after installation, with expertise spanning standard and specialized roofing materials like metal. The company's organized approach, reliable service, and willingness to explain procedures and maintenance make roof replacement a stress-free experience for clients.

"The company that replaced our roof did a great job. They were professional, on time, and paid close attention to every detail. The old roof was carefully taken off, and the new one was put on perfectly. Afterward, the team also cleaned up very well and made sure everything looked great. They told us how it would work and answered all of our questions. The new roof on our house looks great and will last for a long time. We're very happy with the…" — Amy R.
232 Jersey Ave
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-563-1460

Custom Home Improvement & Repairs of Hampton Roads

4.9(1,013 reviews)
24/7 EmergencyOnline EstimatesOpen WeekendsSpanish Speaking
AI Review Summary

Custom Home Improvement earns consistent praise from customers for exceptional communication, professionalism, and quality workmanship throughout every project phase. Clients consistently highlight the team's punctuality, thorough cleanup, transparent explanations of work completed, and proactive problem-solving that addresses long-term concerns rather than applying temporary fixes. The company's seamless coordination—from initial consultation through financing, scheduling, and final inspection—combined with reliable project managers and skilled crews, makes them a trusted choice for roofing and home improvement needs in the Chesapeake area.

"We recently had our roof replaced by Custom Home Improvement here in Chesapeake, VA, and the entire experience was outstanding from start to finish. The roofing crew arrived right on time and immediately got to work. Their professionalism and efficiency were clear from the beginning. Neil, the project manager, quickly identified several trouble spots that could have caused long-term structural issues. Instead of applying a temporary fix, he…" — Dionne W.
2000 General Booth Blvd Ste 204
✓ LicensedInsured - Not confirmed✓ 22 yrs in business

+1 757-720-7032

WT Anderson Roofing & Siding

4.9(633 reviews)
Online EstimatesWomen-OwnedMinority-Owned
AI Review Summary

WT Anderson Roofing & Siding stands out for exceptional professionalism, transparent communication, and superior craftsmanship throughout every project phase. Customers consistently praise their knowledgeable project managers, detailed estimates, punctual timelines, thorough cleanup, and attentive follow-up—treating clients as valued partners rather than transactions. The company delivers outstanding quality work backed by fair pricing, military discounts, and a commitment to customer satisfaction that has earned them loyal recommendations across the Hampton Roads area.

"Bottom line up front, you will not find a better home exterior class A contractor in Hampton Roads period. We received 5 estimates for our siding, fascia, soffit, and gutter replacement and W.T Anderson stood out amongst the rest for their value, honesty, and professionalism. Save yourself time and money and make W. T. Anderson your first and only estimate. W. T. Anderson was a class act from my initial interaction with their estimator…" — Dan P.
4627 Cape Henry Ave
✓ Licensed✓ Insured✓ 20 yrs in business

+1 757-816-9203

Best Roofing Of Virginia

4.9(430 reviews)
Open WeekendsVeteran-OwnedWomen-Owned
AI Review Summary

Best Roofing of Virginia consistently delivers high-quality workmanship and exceptional customer service, with customers praising their thorough problem-solving approach, transparent communication, and competitive pricing. The team—including ownership—demonstrates genuine care for customer satisfaction by taking time to understand unique roofing challenges, explaining their process clearly, and following through on repairs until issues are fully resolved. Customers particularly appreciate their professionalism, punctuality, attention to detail, and willingness to tackle complex or uncommon roofing problems that other companies decline.

"This company will go above and beyond to make sure you are satisifed with your roof! First and foremost, with Best Roofing Company you are going to get a high-quality roof at a fair price. I love the way my new roof looks, and I know it is going to last us for a long time. However, what really impressed me is Best Roofing's ability to tackle uncommon challenges. I came to Best Roofing Company for a roof replacement, but we also had a very…" — Sara C.
320 33rd St #1451
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-463-2378

AI Review Summary

Marc's Pressure Cleaning earns consistent praise for exceptional attention to detail and genuine care for customer property, with the owner and crew going above and beyond—such as protecting plants and furniture during soft washing and managing runoff meticulously. Customers consistently highlight the company's professionalism, responsiveness, and fair pricing, with Marc personally handling quotes same-day and crews arriving on time to deliver high-quality results that last. The team's expertise in gentle cleaning techniques for delicate surfaces like aged brick and roofs, combined with their honest assessments (such as advising when cleaning isn't necessary), builds strong customer trust and loyalty.

"Marc, the owner along with his crew came out to our house to do a soft wash roofing cleaning, we got a letter from our association. They were on time and did an excellent job, I also saw Marc going around to move patio furniture and my plants that I missed, to make sure nothing got wet or damaged, loved that he cared. Also, good reasonable price and love how clean the roof looked afterwards, we would definitely use them again and recommend them…" — Heike C.
900 Commonwealth Pl Suite 200-316
✓ Licensed✓ Insured✓ 30 yrs in business

+1 757-608-2915

Premier Chimney and Roofing

4.9(353 reviews)
Online EstimatesOpen Weekends
AI Review Summary

Premier Chimney and Roofing earns consistent praise for their thorough, detail-oriented workmanship and exceptional professionalism—customers highlight how technicians go above and beyond to explain their work, maintain cleanliness, and catch issues other companies miss. The team is known for their reliability and responsiveness, keeping appointments, calling ahead, and following up promptly even when parts require extended lead times. Customers repeatedly emphasize the friendly, knowledgeable service and photo documentation that demonstrate quality craftsmanship and give them confidence in the job being done right.

"Premier chimney and roofing this is really a good company when I called them in December. I made an appointment with him and they came out in January. They kept their word I had called other companies which they did not even respond. On my first visit from Premier chimney and roofing technician Ryan Brown and CJ came out very pleasant and kind.First of all, they called me 10 minutes prior to arriving to let me know they were on their way and when…" — Beverly B.
1561 Bradford Rd #101
Licensed - Not confirmedInsured - Not confirmedYears - Not confirmed

+1 757-460-9140

Pyramid Roofing (Peninsula)

4.9(345 reviews)
24/7 EmergencyOpen Weekends
AI Review Summary

Pyramid Roofing Services earns consistent praise from customers for their professionalism, attention to detail, and exceptional workmanship. Clients repeatedly highlight the team's reliability—completing projects efficiently while maintaining spotless job sites—along with transparent pricing, honest communication, and genuine care for customer satisfaction. With a track record of repeat customers and strong recommendations, Pyramid Roofing stands out for delivering quality results that enhance home curb appeal while respecting both budgets and properties.

"I recently had Pyramid Roofing in Williamsburg, VA, handle a full roof replacement on my home, and I couldn’t be more thrilled with the results. From the very first interaction, Mike, our salesman, stood out as a true professional—he listened to all my concerns, provided a detailed quote with no hidden fees, and came through on every single promise he made. His pricing was incredibly competitive, beating out several other bids without sacrificing…" — Justin W.
2350 50th St
Licensed - Not confirmedInsured - Not confirmed✓ 40 yrs in business

+1 757-908-6152

Jayhawk Exteriors

4.9(332 reviews)
24/7 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

+1 757-963-6559

Pyramid Roofing (Southside)

4.9(298 reviews)
24/7 EmergencyOpen Weekends
AI Review Summary

Pyramid Roofing has earned consistent five-star praise for their thorough inspections, knowledgeable staff, and exceptional customer service from initial contact through project completion. Customers particularly appreciate the company's transparency, professionalism, and willingness to educate homeowners about their options, along with the detailed documentation and follow-up care (including magnetic cleanup). With 40 years in business and a lifetime guarantee on their work, Pyramid Roofing stands out for their commitment to quality craftsmanship and building trust with customers who have had previous negative experiences.

"This is a review in 2 parts. Part 1. I bought an older home in 2002 & replaced the roof in 2009. The company that did the work in 2009 was a REALLY bad company, they lied about the work, about the materials they used, and it was a real cluster. The roof they put on had areas with poor quality flashing, areas with no flashing, and an area under a dormer window with a 2-3" gap, open to the elements. Adding insult to injury, they went out of…" — Lylith F.
4580 Village Ave suite A
Licensed - Not confirmedInsured - Not confirmed✓ 40 yrs in business

+1 757-574-9995

Find Roofers Near You in Chesapeake

Why Hire a Local Roofer in Chesapeake?

Local Climate Knowledge

Chesapeake roofers understand Virginia's specific weather patterns and choose materials built to last in local conditions.

Building Code Compliance

Local contractors know Chesapeake's permit requirements and code standards, ensuring your repair passes inspection.

Faster Response Times

A local company can respond to emergencies quickly and follow up easily if issues arise after the repair.

Typical Roof Repair Costs in Chesapeake

Repair TypeTypical Cost Range
Minor Leak Repair$150 – $400
Shingle Replacement (small area)$300 – $900
Flashing Repair$200 – $600
Gutter Repair / Replacement$150 – $500
Section Repair (large area)$1,500 – $5,000
Emergency Repair$500 – $1,500
Full Roof Replacement$8,000 – $25,000+

* Estimates only. Actual costs vary by scope, materials, and contractor. Get at least 3 quotes.

FAQ: Roof Repair in Chesapeake, VA

Roof repair costs in Chesapeake typically range from $150–$400 for minor leak repairs to $1,500–$5,000 for extensive section repairs. Emergency repairs can cost more. The exact price depends on the extent of damage, roofing material, roof pitch, and the contractor you choose. Always get 3 quotes before committing.