Licensed & Insured • Serving Hampton Roads, VA
Roof Repair & Replacement in Hampton Roads, VA
Harbor Guard Roofing provides roof repair, roof leak diagnosis, and roof replacement for Hampton Roads homeowners. We inspect shingles, flashing, gutters, downspouts, and the discharge path so your recommendation addresses how water enters and leaves the home. Brett Mathis brings over 20 years of roofing experience to that conversation.

Free online roof estimate
Get Your Roof Replacement Price Range
Planning a residential asphalt-shingle roof replacement in Hampton Roads? Use our Roofr tool for a preliminary estimate based on aerial roof measurements.
- Enter your property address.
- Follow the roof and contact-information prompts.
- Review your preliminary estimate.
Have your address and contact details ready. An inspection and written proposal define the scope and price. Concealed damage found later may require an approved change to the work. Repairs, metal roofs, gutters, drainage, and storm work need a separate inspection.
Open the Roofr estimator in a full page
Need help with a leak or repair? Request a free inspection or call (757) 239-0707.
Roof, gutter and drainage help
Full water-path protection from shingles to underground drainage
Harbor Guard Roofing helps homeowners move from water worry to a clear plan: inspect the roof, gutters, downspouts and discharge path, explain the options, protect the property, complete the work and walk the job before we leave.
View examples and image disclosuresSee property protectionInspection process
Free Roof and Water Path Inspection
Tell us what you are seeing: a roof leak, storm damage, overflowing gutters, or water collecting near the home. We will inspect the roofline and drainage path, take photos, and explain the next step before any work begins.
Roofing Details and Inspection Examples
These images illustrate roofing, inspection, and property-protection details. They are examples, not documented Harbor Guard projects. See our gallery for image disclosures.



Plan the Full Water Path: Roof, Gutters, and Drainage
Tell us which parts of the system you want reviewed. We can price the roof, gutters, downspouts, and underground drainage together so water is managed from the shingles to the final discharge point.
Virginia Licensed & Insured • Roofing • Gutters • Downspouts • Underground Drainage • Storm & Insurance Claim Help • Financing Available.
Your Harbor Guard contact
Talk with Brett Mathis About Your Roof and Water Concerns
Brett Mathis brings over 20 years of roofing experience to Harbor Guard Roofing and is your contact for roof and water concerns. Tell us about your roof leak, replacement plans, overflowing gutters, or drainage concerns so we can arrange an inspection and explain the next step.
Our inspection process uses photos and a written scope to help you compare repair and replacement options before work begins.
Call Brett and the Harbor Guard team: (757) 239-0707 · About Harbor Guard Roofing · What our inspection covers
Roofing, Gutters, and Drainage Services in Hampton Roads
From a cracked pipe boot leaking into your ceiling to gutters dumping water beside the foundation, we handle the exterior water problems Tidewater homes actually face.
Roof Repair
Missing shingles, flashing problems, pipe boots, and wind-driven rain leaks fixed fast.
Roof Leak Repair
We find the real source of the leak, not just the stain on the ceiling, and stop it.
Roof Replacement
Wind-rated, algae-resistant roofing systems selected for coastal Virginia weather.
Storm Damage
Roof damage assessment, photo documentation for insurance conversations, and temporary tarping when appropriate. Timing depends on weather, safe access, and crew availability.
Siding
Vinyl and storm-damaged siding repair and replacement for coastal homes.
Gutters
Seamless gutters, guards, and downspouts sized for heavy Hampton Roads downpours, with drainage planning when roof runoff needs to move farther away.
Top-to-Bottom Water Mitigation
The roof is only the first part of the water path. Harbor Guard looks at where rain hits, how it leaves the roofline, where the downspouts discharge, and whether underground drainage is needed to move water away from the home.
Learn how roof replacement, gutters and underground drainage work together. Our guide includes a rainfall-volume example, questions to ask before approving work and a free homeowner rain observation checklist.
1. Shingles, Flashing, and Roof Leaks
We start where water first enters the system: shingles, flashing, pipe boots, valleys, vents, and storm-damaged roof areas.
2. Gutters, Guards, and Downspouts
We look at whether roof runoff is being collected, filtered, and sent to downspouts that can handle coastal Virginia rain.
3. Underground Drainage and Discharge
Where appropriate, underground drainage carries collected roof water to a suitable discharge point. A curb outlet to the street is an option where approved; the route, outlet and maintenance access belong in the written scope.
Why Hampton Roads Homeowners Choose Harbor Guard
Coastal Virginia is hard on the whole exterior water system. Hurricane-season wind, nor’easters, salt air near the water, heavy downpours, clogged gutters, and short downspout discharge all leave signs that need a trained eye.
Harbor Guard Roofing is local, organized, and easy to work with. We install wind-rated, algae-resistant roofing systems built for this climate, and we can coordinate gutters, downspouts, and drainage when roof runoff needs a more complete plan. After a storm, we help document roof damage and can meet with your adjuster when appropriate.
The Harbor Guard Promise
Inspect the full water path, explain the options, protect the property, complete the work, clean up, and walk through the finished result. That simple process keeps roofing, gutter, and drainage projects clear and organized.
1. Inspect the Water Path
We inspect the roof, gutters, downspouts, and discharge areas, then explain whether repair, replacement, storm documentation, or drainage work makes the most sense.
2. Protect & Build
We protect landscaping, driveways, siding, and outdoor areas before work begins, then complete the work with an organized crew.
3. Clean Up & Walk Through
We remove debris, magnet-sweep for nails, check the yard and driveway, and walk the finished work with you.
Plan Your Roofing Budget with Confidence
Roof Repairs
$350 to $750+ for common leak repairs, flashing issues, pipe boots, and storm-lifted shingles.
Roof Replacement
$10K to $25K+ for many full, wind-rated roofing systems on Hampton Roads homes.
Roof + Gutters
$13K to $30K+ for a new roof plus seamless gutters, matched and integrated.
Roof + Gutters + Drainage
$16K to $38K+ for roof, gutters, downspouts, and underground drainage.
These are planning ranges, not a guaranteed price. The right plan may be a targeted roof repair, a gutter and downspout upgrade, underground drainage, or a full roof replacement. Financing is available to help spread the cost over monthly payments.
Serving All of Hampton Roads
A local crew that knows Tidewater roofs: salt air at the Oceanfront, wind-driven rain across the Southside, and humidity everywhere in between. We serve Virginia Beach, Chesapeake, Norfolk, Newport News, Hampton, Portsmouth, Suffolk, Williamsburg, Yorktown, and Poquoson, plus Smithfield, Isle of Wight County, Carrollton, Gloucester, Toano, and James City County.
Frequently Asked Questions
Can I get a roof estimate online?
Yes. Start with our online roof replacement estimator for a preliminary residential asphalt-shingle estimate. Have your property address and contact details ready. An inspection and written proposal confirm the final scope and price.
What is Complete Exterior Water Protection?
It means looking at the full path water takes: shingles, flashing, valleys, gutters, downspouts, underground drainage, and final discharge. The goal is to move rainwater away from your home, not just off the shingles.
Do I need gutters or underground drainage with a new roof?
Sometimes. If gutters overflow, downspouts dump beside the foundation, or water collects near the home after heavy rain, it makes sense to evaluate the roof, gutters, and drainage together before choosing a final scope.
How much does a new roof cost in Hampton Roads?
Our published planning range for roof replacement is $10,000–$25,000+. It is not a fixed quote or a regional average. Measured roof area, pitch, materials, tear-off, decking, ventilation, and access affect the scope. See replacement cost factors and what to compare in a written quote, then schedule an inspection for project-specific pricing.
Do you help with storm and insurance claims?
Yes. We document storm damage with photos, provide a written estimate, and can meet your insurance adjuster on site. Claim decisions always belong to your insurer.
Are you licensed and insured in Virginia?
Yes. Harbor Guard Roofing is a Virginia-licensed and insured roofing contractor. We can share license and insurance details before work begins.
Do you offer financing?
Yes. Flexible monthly payment options are available for roof replacement, gutters, and larger exterior water protection projects.
How fast can you respond to a roof leak?
Active leaks get fast attention. When needed, we can tarp first to limit water intrusion while the permanent repair is scheduled.
Ready to Get Your Roof and Water Path Checked?
Book a free photo-based inspection for your roof, gutters, downspouts, and drainage concerns, or see your roof replacement price range online.
Harbor Guard Roofing
Call or text (757) 239-0707 · admin@harborguardroofing.com
Mailing address: 550 First Colonial Rd, Virginia Beach, VA 23451 · Virginia Licensed & Insured