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Best 5 Roof Repair Companies in Chesapeake, VA

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Written By Jessica Hurtault|Last Updated: February 16, 2024

A compromised roof can pose a risk for your Chesapeake property through water damage and other problems. However, finding a dependable roof repair company can be a headache when you need service quickly.

We looked at the customer reviews, cost, and reputation of Chesapeake roof repair companies to create a list of our top picks. See our top picks below.

5 Best Roof Repair Companies in Chesapeake, VA

Wholesale Roofers Logo

Wholesale Roofers

Based on 361 customer reviews.

Services Offered

Solar Panel InstallationSkylightsQuality InspectionFlat RoofsVentilationRoof RepairAsphalt RoofsReplacement


  • Preventive services
  • Transparent pricing
  • Quality customer service
1 Columbus Ctr #600, Virginia Beach, VA 757-424-5981 wholesaleroofersva.com
The Roofing Company Inc. Logo

The Roofing Company

Based on 60 customer reviews.

Services Offered

SlateSkylightsRoof RepairReplacementQuality Inspection


  • Transparent pricing
  • Preventive services
  • Transparent project updates
3640 S Plaza Trail Ste 204, Virginia Beach, VA 757-867-6600 theroofingcompany.com
Stublen Roofing Logo

Stublen Roofing

Based on 110 customer reviews.

Services Offered

Flat RoofsAsphalt RoofsRoof RepairReplacementSlateMetal Roofs


  • Customer education
  • Transparent pricing
  • Transparent project updates
4011 Seaboard Ct, Portsmouth, VA 757-488-8190 stublenroofing.com
DSR Exterior Remodeling Corporation Logo

DSR Exterior Remodeling Corporation

Based on 115 customer reviews.

Services Offered

Flat RoofsVentilationRoof RepairReplacementQuality Inspection


  • Quality customer service
  • Customer education
  • Free inspections
4501 Revere Dr, Virginia Beach, VA 757-534-8240 drroofingcontractorllc.com

More Local Roofing Companies

Infinity Roofing & Siding

User Reviews: 4.6/5 

4445 Corporation Ln Ste. 165
Virginia Beach, VA 23462

Gilpin Roofing Inc.

User Reviews: 4.6/5 

5051 Euclid Rd
Virginia Beach, VA 23462

Jayhawk Exteriors Inc

User Reviews: 4.5/5 

1824 Engle Ave
Chesapeake, VA 23320

Exterior Source

User Reviews: 4.5/5 

1429 Crossways Blvd Ste B
Chesapeake, VA 23320

Pyramid Roofing

User Reviews: 4.5/5 

2635 Arkansas Ave
Norfolk, VA 23513

Bayview Exteriors LLC

User Reviews: 4.3/5 

1170 Lance Rd #108
Norfolk, VA 23502

United Exteriors

User Reviews: 4.2/5 

1300 Diamond Springs Rd UNIT 302
Virginia Beach, VA 23455

Andrews Roofing Co Inc

User Reviews: 4.2/5 

757 Mt Vernon Ave
Portsmouth, VA 23707

Hometown Remodeling

User Reviews: 4.5/5 

3200 Dam Neck Rd #102
Virginia Beach, VA 23453

To share feedback or ask a question about this article, send a note to our Reviews Team at reviewsteam@thisoldhousereviews.com.

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Common Types of Roofing Problems

Chesapeake roofing companies can fix roof problems such as a leaking roof, standing water, storm damage, clogged gutters, and poor ventilation. Read on for more about the most common roofing problems.

Roof Leaks

Roof leaks are a common issue among homeowners, and they can happen for several reasons. Your homeowners insurance might pay for repairs if the cause is not age or poor maintenance. Putting off repairs can turn a minor leak into a major and expensive issue. Water damage near your skylights, flashing, chimney, vents, or gutters is a common sign of a leak.

Standing Water

Flat roofs are most likely to get standing water, but it can happen on any roof type. Pooled water that doesn't drain off your roof results in consistent moisture in parts of the roof. This moisture can cause algae, mold, rot, and mildew over time. Eventually, the water can seep into your home's support structure, leading to damage, a sagging roof, and health risks for your family.

Storm Damage

Severe storms can lift shingles and result in damage to your roof.

While a couple missing shingles may not seem important, shingles protect your roof from water and debris. Without that protection, your roof is more susceptible to wear and tear over time. Compromised flashing is another common problem after storms. If damaged, the seams that secure your roof and any protruding structures separate. This leads to several moisture problems.

Clogged Gutters

Clogged gutters can create issues for them and your roof. The longer you don't address the blockage, the more water builds up in your roof system. Excess debris can result in leaks in your roof and harm to fascia boards.

Poor Ventilation

Proper ventilation is important for controlling humidity and enabling proper circulation. Insufficient ventilation leads to issues with mold formation, maintaining your home temperature. It can cause damage to rafters, insulation, sheathing, and shingles. It may also lead to higher energy bills, and occupants may experience health issues.

Factors To Consider When Choosing a Roof Repair Company in Chesapeake

Fixing your roof can be a major expense. We suggest weighing the following criteria when deciding on Chesapeake roofing companies:

  • Cost and payment options: Get quotes from different companies to compare. Make sure you understand the terms and what you’re paying for. Get any financing agreements in writing.
  • Material quality: Find out what kind of materials they'll use. Roofers shouldn’t cut corners when doing a repair.
  • Past project photos: Ask for before and after photos to verify skills and experience.
  • Qualifications: Ask the roofing contractor for proof of proper licensure and insurance before they start any work.
  • Reputation and reviews: Look at reviews on the Better Business Bureau, Trustpilot, and Google Reviews to get customer insights and see if the company has had any legal issues.
  • Safety measures: Roofing work requires preventative safety measures. The company you select is responsible for everyone on the jobsite. This is another reason to prioritize proper certifications and insurance, so the burden is on the company if someone is injured.
  • Timeline: Talk about timeline expectations and get commitments in writing before starting any work.
  • Warranty: Reputable roofing contractors provide materials and labor warranties. Verify the roofer is authorized since most shingle manufacturers only honor warranties if authorized dealers install them.

How Much Does It Cost To Repair a Roof?

Don't put off roof repairs until a replacement is needed, since fixes usually cost less. Chesapeake homeowners pay an average of $877 for roof repairs. Factors such as repair type, pitch, materials, roof features, and location determine your final cost. Small holes and replacing a few shingles are on the lower end, while a sagging roof and a full roof replacement are on the higher end.


CDC Wonder

U.S. Census

U.S. Bureau of Labor Statistics

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Frequently Asked Questions About Roof Repair in Chesapeake

How long does it take to repair a roof?

How long a roof repair takes is based on the issue and scope. Most roofers can finish residential roofing repairs in 12 days, but commercial roofing projects may take longer if the building is bigger.

What kind of license should a roofing contractor have?

Some states require either a roofing or general contractor license through the Contractors State License Board. Roofers may also require a license at the local level, even if your state doesn't.

What should you do if your roof starts leaking?

Contact a professional roofer as soon as a leak occurs. Don’t attempt to release the leak yourself. Have a contractor come survey your roof and fix the issue immediately.

What’s the best roofing material?

Slate, cedar, concrete, metal, and clay are the most durable and long-lasting roofing materials. The most popular roofing material in Chesapeake is generally asphalt shingles. Ask a roofing specialist to recommend the right material for your home and location.

How can you tell if a roofing company is legitimate?

Any trustworthy roofer will have no issue showing it's licensed, bonded, and insured. Many quality providers obtain a license with the local Roofing Contractors Association. Checking customer reviews and looking at photos of previous work can also help you vet the company.

To share feedback or ask a question about this article, send a note to our Reviews Team at reviewsteam@thisoldhousereviews.com.