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TRUSTED BY CHESAPEAKE, VA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon1.9k+
    Verified roofing services reviews

Top-Rated Roofers in Chesapeake - Updated Nov 2026

Avatar for W.T. Anderson Corp
W.T. Anderson Corp
4.9(
341
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or Replace

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2001

Free estimates

Warranties offered

"I highly recommend W.T Anderson for any roofing need for the follow reason. The five member roofing crew arrived early Monday morning and began to go to work. The on-sight supervisor introduced herself and provided me with her phone in case I had questions or concerns. Every team member was assigned a task and worked efficiently with little wasted effort. The team remained focus on the job at hand even when the sight supervisor was not present (which was not often or long). The company’s owner made sure to visit the sight throughout the day. His enthusiasm and positivity for the job was mirrored by all at the job sight. The job consisted of removal of 2 layers of shingles, remove and re-install 3 Solar Tubes, replace 3 vent covers (2 bathroom and 1 kitchen), installed 3 Easy Sleeve pipe flashing (a product I recommend, made by a local Virginia company), replacing of 11 sheets of roof sheathing (a lot of water damage during the 30+ years since the first layer was installed, not surprised), installed Weather Watch leak barrier along eaves, rakes, around chimney and all roof penetrations, install underlayment and finally the shingles. I was expecting the job to take 2 days (especially after the water damage was found). However, the job was done in one day and the dumpster was picked up the next day. I cannot express how impressed I am with the thoroughness with which the clean-up was done. I climbed on the roof and inspected the work I was quite pleased with the overall job. I did find one discrepancy (one of the Easy Sleeves was installed incorrectly). Once the company was informed the owner can out the next day to see for himself. He tried to fix it right then and there, but was unable to. The next day the crew was out to remove and replace (with new material) the Easy Sleeve. I am absolutely happy that I chose W.T Anderson for my roofing project. Although their quote was not the lowest, the combination of good reviews and the positive impression I had after the owner’s visit to formulate a bid was central in the selection (I had four roofing quotes). They were very responsive during the whole process (bid, work and follow up) and I would highly recommend them."
Timberline Solar
Timberline Solar Roofing
Timberline Solar Roofing
Additional Photos
Additional Photos

+33

Response time1 day
Response rate100%
15 neighbors recently requested a quote
Avatar for Princess Anne Contracting Inc
Princess Anne Contracting Inc
5.0(
58
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 1997

Free estimates

Emergency services offered

"Dave Lobur and Princess Anne Contracting exceeded my expectations. They did a quality install, in a timely manner. Dave was on site majority of the time and his employees were professional. I had the house wrapped after the roof went on and two wrap contractors commented on how well the roof was installed."
3 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Jayhawk Exteriors Inc
Jayhawk Exteriors Inc
4.6(
429
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2003

Free estimates

Warranties offered

"Our roof was over 20 years old and we discovered a leak. I got quotes from two companies but once I met James and he explained my quote I didn't need any additional information I wanted Jayhawk to do our roof. The crew started in the morning and they finished by the afternoon with both our house and the exterior garage and it looks great. This whole process took about 2 weeks and I could not be pleased."
After new roof, siding and windows
After new siding, soffit and trim
After new siding, soffit, trim wrap, gutters and shutters
What a transformation!  New vinyl siding, soffit, trim, stone and porch posts
New roof, siding and trim

+56

Response time1 day
3 neighbors recently requested a quote
Recommended by94%of homeowners
Avatar for Nansemond River Roofing & Siding, LLC
Nansemond River Roofing & Siding, LLC
4.9(
41
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For BusinessFlat, Foam or Single Ply Roofing - Repair+1 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2013

Emergency services offered

Warranties offered

"After a hurricane in July, our 5000 square foot 20 year old roof was in bad shape on the back side. We reached out to Steve (owner @ Nansemond) and he informed us the roof was built as a 30 year roof and the damage incurred was not normal wear. Because of this, we filed a claim with progressive ASI insurance. Initially the insurance company wanted to replace 2 slopes and was willing to pay about 4500$ in damages. After Natalie sent in paperwork and after a little patience, the insurance company decided to replace the entire roof at a cost not including deductible of about 19k. Steve promptly gave us options and got his guys out here to replace our roof. The insurance company only wanted to put roll-on material on the back flat roof over the huge porch but due to the fact he did not want to put in a subpar product that would fail, they upgraded it to TPO product which is top of the line in this application. In total with rotting boards and deductible we now have a 25k roof upgrade and we are out a total of 2,000$. Steve was reachable throughout the process and answered his phone any time I called, which speaks volumes to the care he puts into his company. Anybody who mentions their roof near me will hear about my positive experience with this company, I wish more people cared as much about their customers as Steve."
New roof
New roof
New roof
Roof repair
New roof

+24

Response time1 day
Response rate92%
Recommended by97%of homeowners
Avatar for Roof Shark, LLC
Roof Shark, LLC
5.0(
23
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2023

Free estimates

Credit card accepted

"Nick with Roof Shark was very personable, explained the whole process and his company is quite efficient. They covered up our landscaping and removed all of the debris. I loved that he checked back with us to make sure we were happy!! I would and have recommended him to people that need a new roof or roof repair."
Osvaldo’s Roof Repair
Osvaldo’s Roof Repair
Osvaldo’s Roof Repair
Osvaldo’s Roof Repair
Osvaldo’s Roof Repair

+8

4 neighbors recently requested a quote
Avatar for Quality Built Exteriors
Quality Built Exteriors
4.2(
273
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceNatural Slate Roofing - Repair+26 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2005

Free estimates

Emergency services offered

"Mr. Johnson came out and took a look at our roof and gave an excellent quote for the work to be done and a time within a few weeks as the weather was warming for it to cure. The crew were very quick about prepping things and then went about applying the sealant needed for the mobile home. When done, they cleaned up and even blew down the yard of any debris from the gutters. A wonderful job all around."
We can contour your wood fence into your trees so you have an artwork instead of removing the tree
Additional Photos
Vinyl privacy fence
Roof Replacement
Additional Photos

+15

Response time9 hrs
Response rate100%
16 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
388
)
Asphalt Shingle Roofing - Install or Replace

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

Elevate your home with Home Genius Exteriors, setting the standard by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+76

192 neighbors recently requested a quote
Recommended by96%of homeowners
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Showing 1-10 of 460
Roofing FAQs, answered by experts

Working with roofing contractors in Chesapeake, VA, provides immediate benefits like improved protection from severe weather and enhanced energy efficiency during humid summers. Over time, a professionally installed roof helps prevent water intrusion, reduces the risk of structural damage, and can lower ongoing maintenance needs. Upgrading your roof also supports better insulation and can contribute to long-term property value retention.

Helpful?

A new roof installed by reputable roofing contractors in Chesapeake, VA, can significantly enhance your home’s resale appeal. Buyers value recent roof replacement, especially when it includes storm-resistant features and improved insulation. These upgrades can help your property stand out, reduce potential insurance concerns, and reassure buyers that the home is protected against Chesapeake’s challenging weather conditions.

Helpful?

Chesapeake’s humid subtropical climate, with hot summers and frequent storms, means roofing contractors must prioritize wind-resistant materials and moisture control. Hurricane season increases the need for durable roof installation and proper attic ventilation. Scheduling roof repair or replacement in spring or fall helps avoid weather-related delays and ensures materials perform well against local heat, humidity, and heavy rainfall.

Helpful?

Roofing contractors in Chesapeake, VA, include specialists in residential roof repair, roof replacement, and storm damage restoration. Some focus on flat or low-slope commercial roofing, while others are experts in metal, slate, or asphalt shingles. Many contractors also offer gutter installation, solar roofing, and historic home restoration, allowing homeowners to address multiple roofing needs with one experienced team.

Helpful?

Homeowners in Chesapeake may encounter unexpected costs such as replacing damaged roof decking, upgrading attic ventilation, or addressing issues revealed during roof repair. Weather delays, especially during hurricane season, can extend project timelines. Additional expenses might include permits, inspection fees, or premium materials needed for salt air resistance. Gutter replacement and landscape protection are also common considerations during roofing projects.

Helpful?

The Chesapeake, VA homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.