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Top-Rated Roofers in Chesapeake - Updated Nov 2026

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+25 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 1997

Free estimates

Emergency services offered

"Dave at Princess Anne Contracting is personable and professional; certified and ethical. A few months ago, I had a small roof leak after a storm. I had contacted a different company and they tried to take advantage of me. The dishonest company quoted me $7,000 and said the back half of the roof needed to be replaced. I knew this was false because I had a home inspection two months earlier and the inspector said the roof had several years left. I contacted Princess Anne Contracting based on a neighbor’s recommendation. Dave promptly came out and quickly identified the problem - a small piece of flashing had come loose. Dave immediately fixed the flashing, also fixed a shingle he noticed was coming loose and even cleaned out a gutter that he noticed had some debris in it. It only cost $125. Dave saved me $7,000 dollars that the unethical company tried to charge. Dave assured me that the roof still had several years before it needed to be replaced. And, I’m happy to say that several months later, Dave’s repair held up like a champ while the remnants of Hurricane Ian passed through last night! Quality work at an affordable price. I highly recommend Princess Anne Contracting!"
4 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+25 more

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2003

Free estimates

Warranties offered

"Everything went smoothly. They were on time. Worked very efficiently. They also included our shed roof in the price. They were the best quote we got for the work we wanted done. There was no mess left behind. The roof looks great. My husband and I were so pleased with the roof that we had them come back out several weeks later to put new gutters on the house."
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 Home Genius Exteriors
Home Genius Exteriors
4.9(
436
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or Replace+2 more

Serving Chesapeake, VA and surrounding areas

Approved

Super Service Award Winner

In business since 2004

Free estimates

Emergency services offered

"Recently had my roof replaced by Home Genius. Everyone from the sales representative Andre to the project manager AJ M and the roofing crew were courteous, kind, respectful and very thorough in addressing the needs required to repair my roof. I highly recommend!"
Roofing
Roofing
Roofing
Roofing
Roofing

+84

519 neighbors recently requested a quote
Recommended by90%of homeowners
Avatar for Quality Built Exteriors
Quality Built Exteriors
4.2(
273
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceNatural Slate Roofing - Repair+25 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

288 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for United Exteriors, LLC
United Exteriors, LLC
4.4(
64
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For Business+7 more

Serving Chesapeake, VA and surrounding areas

Approved

Super Service Award Winner

In business since 2006

Free estimates

Warranties offered

"We hired United Exteriors, LLC for a small roofing job replacing roof fans, Bill Johnson came by to survey work I needed, and made several recommendations about our roof that needed to be addressed. He offered us a reasonable quote to install a cricket , fix some flashing, as well as the roof fans I needed replaced. He was able to do the job within a week, which took about, 1/2 a day to complete. He was also able to match the color of our existing roof shingles. The finished job looks awesome. Overall, I was impressed, especially after calling other companies that would not take the job or stated that I would have had to buy their fans to do the work. I would highly recommend them and use them again if needed."
Beach house re-roof
Re-roof before
Rustic Blend
New roof
Asphalt shingle re-roof

+4

Response time2 days
Response rate88%
58 neighbors recently requested a quote
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FAQs for roofing projects in Chesapeake, VA

Maintaining your soffit is essential. You must inspect it twice yearly to catch any clear signs of deterioration. Look for cracks, mold, rotted wood, sagging sections, chipped paint, or missing boards. If these issues are detected, contact a professional immediately to repair or replace the damaged soffit and protect your home’s structural integrity.

To maintain your fascia boards and soffits, inspect them regularly to protect your roof and home's structure. Clean your gutters to remove debris and prevent moisture buildup. Repaint any damaged sections to keep moisture at bay. Upgrading drip edges and vents improves airflow and dispels moisture efficiently, helping you avoid severe damage and costly repairs.

While installing a new soffit over an existing soffit isn't common, it may be necessary in some older homes. If removing the original soffit could damage delicate structures, a professional might recommend installing the new soffit without complete removal. Always consult a qualified professional to assess the condition and ensure this method is safe and effective.

When hiring someone for soffit and fascia repair, choose a specialist with proven roofing and gutter systems expertise. A knowledgeable contractor will thoroughly inspect your home and provide a straightforward repair or replacement plan. Check online reviews and ask for references to ensure you receive high-quality service that delivers lasting results and strong protection for your home.

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.