Compare top-rated roofing & gutters providers in Chesapeake. Profiles include verified reviews, service details, and direct contact options.
From $50
Up to $500
Open 9:00 AM – 4:30 PM
At Dream Home Solutions in Chesapeake, we transform your living spaces into your dream home. Specializing in roofing, bathroom remodeling, deck bu…
From $50
Up to $500
Open 24/7
In the heart of Chesapeake, we are 5Estimates.com - your comprehensive home services hub specializing in roofing and more. We take pride in servin…
From $50
Up to $500
Open 24/7
At Clark Roofing & Siding Inc in Chesapeake, we specialize in comprehensive home improvement services, transforming your roof and exterior to perf…
From $50
Up to $500
Open 7:00 AM – 5:00 PM
At WT Anderson Corporation Roofing & Siding in Chesapeake, we specialize in comprehensive roofing solutions. Our expertise encompasses various roo…
These companies are based in nearby cities and serve Chesapeake.
From $50
Up to $500
Open 7:00 AM – 5:00 PM
In the heart of Virginia Beach, we are Tidewater Regional Contracting- TRC LLC. Specializing in Roofing & Gutters, our focus is on delivering exce…
From $50
Up to $500
Open 7:00 AM – 5:00 PM
At WT Anderson Roofing & Siding in Norfolk, we specialize in comprehensive home improvement services, focusing on roofing, siding, solar energy, s…
From $50
Up to $500
Open 8:00 AM – 4:00 PM
In homes across Virginia Beach, a reliable partner stands by to tackle your roofing and siding needs - we are Custom Contracting, specializing in …
From $50
Up to $500
Open 7:00 AM – 11:00 PM
At JES Foundation Repair in Virginia Beach, we specialize in comprehensive home improvement services, focusing on roofing and waterproofing soluti…
From $50
Up to $500
Open 24/7
At A & S Contractors in Norfolk, we specialize in roofing services, transforming homes with our expert craftsmanship and demolition skills. We're …
From $50
Up to $500
Open 7:30 AM – 4:00 PM
At Stevens Roofing Corporation in Norfolk, we specialize in comprehensive roofing solutions for homes. Our skilled team tackles everything from le…
From $50
Up to $500
Open 8:00 AM – 5:00 PM
In the heart of Virginia Beach, we at Convert Roofing specialize in comprehensive roofing solutions for local homeowners. Our expertise extends be…
From $50
Up to $500
Open 24 hours
At Matrix Construction of Hampton Roads, Inc., we specialize in delivering robust and reliable roofing solutions for homeowners across Norfolk. As…
From $50
Up to $500
Open 7:00 AM – 10:00 PM
In the heart of Virginia Beach, we're Titan Roof - your reliable partner in roofing services. Specializing in roofing and gutters, our team of ski…
From $50
Up to $500
Open 24/7
In the heart of Virginia Beach, we are All Aspects Construction - your reliable roofing contractor. We understand that a leaky roof can cause unwa…
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We show only active businesses that pass moderation. Results are specific to Chesapeake and nearby service areas, and inactive profiles are removed to keep the list current.
Ratings and reviews come from customers who used the service. Compare roofing & gutters pros in Chesapeake by experience, responsiveness, and value before you reach out.
Filter by neighborhood, check locations on the map, and find providers close to home or work in Chesapeake. Listings are refreshed regularly — October 2026.
The same listings in the closest cities — providers there often take jobs in Chesapeake too. Mileage is the approximate distance from Chesapeake.
Looking for roofing & gutters in Chesapeake? This page lists verified local providers with ratings, reviews, and contact options. We show active businesses only — profiles are moderated and updated by owners.
Compare pros by experience, price range, and customer feedback. Many providers offer free estimates or same-day service for common requests. Use filters and the map to find someone close to your address.
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Fantastic company. Really easy estimate process and quick scheduling. They completed the work (vinyl wrapping all soffits, fascia, windows, porch, and all other exposed wood) 2 days ahead of schedule and to a high standard. Workers worked extended hours to meet deadlines and were very respectful to the property. Don’t hesitate if on the fence to hire WT Anderson.
Really pleased with every aspect of this job WT Anderson were professional and courteous throughout. They communicated clearly every step of the way. I have an extensive amount of landscaping on my property and they went above and beyond to insure nothing was damaged. I would highly recommend them
Great experience working with WT Anderson! From meeting with Jon to get an estimate, to responding to issues presented by the HOA, and their patience as to how long it took to get an approval to move forward, WT Anderson was patient and wonderful to work with. We will definitely call on them again. Installed GAF shingles with great warranty for shingles and workmanship. They also replaced rake boards that needed replacing. It looks so much better.
Excellent staff. Made the process easy and we very skilled and professional. Highly recommend this company.
I have had a less than desirable experience with Clark Roofing. I had no trouble making an estimate appointment. I called on 4/19, and my estimate was scheduled a week later on 4/26. I am seeking to have my 100 year old metal roof completely replaced. Barry arrived on time, was very personable, knowledgeable, and helpful. He had samples and some good suggestions about my metal roof replacement. I was impressed and eagerly awaiting my estimate. After not hearing from him for about a week, I called the office and spoke with Gina in Sales. She said she would pass along the request. After two more phone calls, last Thurs (5/11) we realized she’d inadvertently written my phone number incorrectly by one digit. Okay, things happen like that. I additionally gave her an alternate email address, just in case. Yesterday, 5/14, I made numerous phone calls to the office only to receive the voicemail every time. I left a message. I called again today. No answer in Sales, Service, or Billing. I left another message in Sales. Literally immediately after leaving the message, I received the following email from Barry: “Good afternoon Mrs. Duff. Sorry for the delay. Right this moment we do not have the manpower to take on a project this large. We are out a few months on projects now.” He didn’t even include the estimate so that I, as the customer, could make the decision on whether or not I was willing to wait a few months to have the work done. I have never in my life had any business basically tell me that they don’t want my business; and metal roofs are expensive business. I am understandably upset at this point. I have now waited three weeks for an estimate they seem unwilling to provide. I can understand the scheduling issue, this is busy season for roofers, but this information would have been nice to know when Barry came to do the estimate; or at any point over the past three weeks. Even Gina could have reiterated that message two weeks ago and quit wasting my time. I’m unhappy that they have wasted three weeks of my time. I could have made a choice of roofer before now had I not been waiting on their estimate. My wasted time included the 30-45 minute initial meeting for the estimate and a total of 10 phone calls over 3 weeks that included the phone being answered only 3 times and 2 voicemail messages before finally hearing from them. I would not recommend Clark Roofing.
Using GPS data feeds, Clark Roofing and Siding has superior, detailed job-site estimating for materials costing and bid pricing accuracy, plus an effective computer-based manufacturer’s products presentation, giving ease to understanding the features, advantages and benefits. They began the work when scheduled and their experienced work crews completed the job with quality installation knowledge and professionalism. Follow up and final inspection responsiveness has been prompt. This company is a first-class run business. They know how to serve customers’ expectations!
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