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This video shows the team, office building, roof replacement process, and the new roof, no mess technology for Holloway Roofing.

AWARD-WINNING ROOFING SERVICES IN Winchester, VA High-Quality, Innovative Roofing Solutions for Your Home or Business

Why compromise? Choose Holloway Roofing and experience The Holloway Difference!

Roofing Made Easy

  • Free Roof Inspection & Consultation
    One-on-one roofing consultation with our roofing experts, for FREE!
  • Review, Revise & Finalize Project Agreements

    We make financing projects and insurable loss claims a breeze!

  • Schedule & Deliver Your Roofing Project

    Work is always scheduled on a first-come, first-serve basis. Upon contract closure, your production date will be secured!

Need Service Outside of Winchester? We've Got You Covered! Call (540) 924-1553 to Make an Appointment!
  • Afton
  • Arrington
  • Augusta County
  • Augusta Springs
  • Barboursville
  • Bridgewater
  • Broadway
  • Buena Vista
  • Bumpass
  • Charlottesville
  • Churchville
  • Craigsville
  • Crimora
  • Crozet
  • Dayton
  • Deerfield
  • Earlysville
  • Edinburg
  • Elkton
  • Fairfield
  • Fishersville
  • Fork Union
  • Fort Valley
  • Free Union
  • Fulks Run
  • Gladstone
  • Gordonsville
  • Goshen
  • Greenville
  • Greenwood
  • Grottoes
  • Harrisonburg
  • Hinton
  • Hot Springs
  • Ivy
  • Keezletown
  • Lexington
  • Linville
  • Louisa
  • Luray
  • Lyndhurst
  • McGaheysville
  • Middlebrook
  • Middletown
  • Mount Crawford
  • Mount Jackson
  • Mount Sidney
  • Mount Solon
  • Nellysford
  • New Market
  • North Garden
  • Orange
  • Palmyra
  • Penn Laird
  • Port Republic
  • Quicksburg
  • Rhoadesville
  • Rockingham County
  • Ruckersville
  • Scottsville
  • Shenandoah
  • Shipman
  • Singers Glen
  • Somerset
  • Stanardsville
  • Stanley
  • Staunton
  • Staunton
  • Steeles Tavern
  • Stephens City
  • Stephens City
  • Strasburg
  • Stuarts Draft
  • Swoope
  • Swoope
  • Timberville
  • Toms Brook
  • Troy
  • Unionville
  • Verona
  • Waynesboro
  • West Augusta
  • Weyers Cave
  • Winchester
  • Woodstock

Roof Repair in Winchester, VA

Protect Your Home When Your Roof Starts Leaking

When a roof starts leaking, every rainfall can feel stressful. Water stains on ceilings, damp attic insulation, and missing shingles can quickly turn into damaged walls and ruined belongings if the problem is not addressed. If you need reliable roof repair Winchester homeowners can count on, Holloway Roofing is here to help.

We provide detailed roof inspections, straightforward recommendations, and repair work that focuses on protecting your home for the long term. Our team is fully licensed and insured as a Class A Contractor in Virginia, and we are certified as a GAF Master Elite Contractor and CertainTeed SELECT ShingleMaster. That means your roof is handled by a company that meets some of the highest standards in the roofing industry.

Based in Harrisonburg and serving Winchester and the wider Shenandoah Valley, we respond promptly, explain what we find in clear terms, and offer free, no obligation estimates so you can move forward with confidence.

Need roof repair in Winchester, VA? Call Holloway Roofing at (540) 924-1553 or send us a message online today.

Why Homeowners Trust Our Roof Repairs

Choosing the right roofing company feels important when water is getting into your home. You want to know your contractor is qualified, established, and committed to doing the job correctly the first time. At Holloway Roofing, we work to earn that trust from the first conversation through the final cleanup.

We hold GAF Master Elite Contractor status, a distinction that only a small percentage of roofing companies nationwide achieve. We are also a CertainTeed SELECT ShingleMaster. These certifications reflect ongoing training, thorough installation practices, and careful attention to manufacturer requirements. Because of this, we can offer powerful manufacturer backed warranty options on qualifying projects.

Our company is fully licensed and insured in Virginia as a Class A Contractor, and we maintain an A+ Rating with the Better Business Bureau. We have been recognized with the GAF President’s Club Award and have been voted one of the top roofers in the Shenandoah Valley. These independent recognitions support what many homeowners already feel after working with us, that we communicate clearly, show up when we say we will, and follow through on our commitments.

We are a family owned roofing company that lives and works in the Shenandoah Valley, regularly handling roof repair services Winchester homeowners and small business owners rely on. Our crews take care around landscaping, protect walkways, and perform thorough cleanup so your property looks neat when we leave. When you call us, you are working with a local team that plans to be here to support your roof for years to come.

Signs Your Roof Needs Prompt Repair

Many homeowners are not sure when a roof problem is serious enough to call a contractor. Some issues are easy to see from the ground, while others show up first inside the home. If you notice any of the following, it is a good time to schedule an inspection for house roof repair Winchester properties often need after storms or seasonal wear.

Common warning signs to watch for include:

  • Shingles that are missing, cracked, curled, or losing large amounts of granules.
  • Damaged or loose flashing around chimneys, skylights, or roof vents.
  • Dark streaks, moss, or areas where the roof surface looks uneven or sagged.
  • Water stains on ceilings or walls, especially after heavy rain.
  • Damp or moldy odors in the attic, or visible moisture on rafters and insulation.

Here in the Winchester area, roofs handle intense summer storms, winter snow, and frequent freeze and thaw cycles. Small openings in shingles or flashing can widen with changing temperatures, which allows more water to enter over time. Catching problems early often means a more straightforward repair and less chance of structural or interior damage.

When we come to your property, we look at the visible roofing, the condition of penetrations like pipes and chimneys, and when practical, the attic or upper interior. This helps us understand not only where water is entering, but also whether the roof deck or insulation has been affected. You receive a clear explanation of what we find, along with photos that show the areas of concern.

Our Roof Repair Process

Not knowing what to expect can make roof issues feel more stressful than they need to be. We follow a consistent process so you always know what is happening and why. From the first call to final inspection, our goal is to make roof repair straightforward and predictable.

It starts with a free inspection. When you contact us, our office works with you to schedule a convenient time for a site visit in or around Winchester, VA. On the day of your appointment, our roofing professional will walk the roof when conditions allow, evaluate problem areas, and check related components such as gutters and flashing. When appropriate and safe, we may also look in the attic to see how far moisture has traveled.

After the inspection, we review our findings with you in plain language. We outline what is causing the issue, whether it is wind damage, aging materials, improper past repairs, or something else. You receive a written estimate that explains the recommended repair scope, materials, and projected cost. If there are multiple options, for example a temporary repair versus a more comprehensive fix, we talk through the pros and cons so you can choose what fits your situation.

Our team performs roof repair work on asphalt shingle systems, metal roofs, and many low slope or flat roofing materials used on homes and smaller commercial buildings. For each project, we protect landscaping as needed and take care to minimize disruption to your property. While work is in progress, we keep you informed about timing, any findings we uncover once shingles or membranes are removed, and how those findings may influence the final repair plan.

Cleanup is not an afterthought. We collect roofing debris, check for nails using magnets where appropriate, and leave the work area tidy. Before we leave, we are available to answer your questions about what was done and how to monitor the repaired area over time.

Roof Repair Decisions & Long Term Protection

One of the biggest concerns homeowners share is whether a repair is enough or if it is time for a full replacement. Our job is to provide a careful assessment so you can make that decision with real information. We consider the age of your existing roof, the extent and location of damage, the type of roofing material, and how many previous repairs have been made.

In some cases, targeted roof repair provides reliable protection, especially when the overall roof is in good shape and the issue is contained to a defined area. In other situations, particularly when the roof is near the end of its expected life or damage is widespread, we may recommend replacement as the more cost effective long term option. If both paths are reasonable, we explain that and respect your decision.

For all our repair work, we use materials from trusted manufacturers such as GAF. Our certifications with GAF and CertainTeed mean we follow established installation methods that help repairs stand up to the four distinct seasons we see across the Shenandoah Valley. When repairs are part of a larger qualifying project, we can offer strong manufacturer backed warranties that provide additional peace of mind.

Storm related damage often involves insurance. While each policy and carrier handles claims differently, we assist by documenting the condition of the roof and providing detailed repair scopes and invoices that you can share with your insurer. Our goal is to give you the information and workmanship you need so your home remains protected through future storms.

Frequently Asked Questions

How quickly can you fix a roof leak at my home?

Response time depends on the severity of the leak and our current schedule, but we work to see active leaks as quickly as possible. We start with a prompt inspection in the Winchester area, then prioritize repairs that are needed to help prevent ongoing interior damage.

How will I know if my roof can be repaired instead of replaced?

During our inspection, we look at roof age, overall condition, and how extensive the damage is. Then we walk you through what we see and explain whether repair, replacement, or both are reasonable options. You receive clear information so you can choose what fits your home and budget.

What should I expect to pay for roof repair?

Costs vary based on factors such as roof type, access, and how much material needs to be replaced. We provide a free written estimate that outlines the specific repair scope and price before any work begins, so you understand the investment and there are no surprise charges from our team.

How do you protect my yard and clean up after repairs?

We take care to protect landscaping and outdoor spaces during roof repairs. Our crews use appropriate coverings where needed, handle debris carefully, and check for nails with magnets when practical. Thorough cleanup is part of every job, and we aim to leave your property neat when we are finished.

Do your roof repairs come with any warranties?

We use quality, warrantied materials from manufacturers like GAF, and certain projects qualify for enhanced warranty coverage based on the scope of work. During your estimate, we explain what warranties apply to your specific repair so you know how your home is protected over time.

If you are concerned about a leaking or damaged roof, you do not have to sort it out alone. Holloway Roofing provides detailed inspections, honest guidance, and a dependable roof repair company Winchester homeowners can turn to when they need to protect their homes. We are ready to look at your roof, explain your options, and help you choose a practical path forward.

To schedule a free roof assessment and estimate, contact our team today. We will review your roof’s condition, answer your questions, and recommend repairs that focus on long term protection, not quick fixes.

Call (540) 924-1553 to schedule your roof inspection.

We Always Strive for Five Stars!

Check Out Our Reviews

At Holloway Roofing, your satisfaction is our priority! See for yourself what our customers have to say about working with us.

    “Great Experience!”
    “They did an outstanding job and you could tell they take pride in their work.”
    - Kayla S.
    “Highly Recommend!”
    “Hard-working guys and didn't cut corners. Will be using them for other projects in the future.”
    - Foster K.
    “Best in the Valley!”
    “Great work and excellent customer service!”
    - Emilee L.
Experience the Holloway Difference!

Get Peace of Mind

Contact Your Local Roofing Experts Today!

Use the form below or give us a call at (540) 924-1553.

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Our Credentials

Backed by Industry-Leading Certifications
  • BBB A+
  • GAF Master Elite
  • Over 10 Years Service
  • Catch-All Roofing System
  • Velux Certified Installer
  • New Roof, No Mess
  • GAF Presidents Club
  • Top Rated local roofing contractor
  • SVB
  • harrisonburg chamber of commerce
  • american owned
  • triple
  • trust
  • financing
  • top rated
  • We Offer Financing! Helping You Get the Roof You Deserve

    A new roof is a big investment! That's why we provide a variety of financing options to help make the buying process easier.

  • The Holloway Difference Don't Do It Their Way, Do it Holloway!
    At Holloway Roofing, our workmanship, materials, professionalism, equipment, warranties, training, and certifications set us apart from the rest!
  • New Roof, No Mess®! Keeping Your Property Safe
    THE EQUIPTER RB4000 is a state-of-the-art roofing debris containment system that is designed to help protect what matters most.
  • Referral Rewards Earn Up To $100 with Each New Referral!

    Once You Do Business with Us, You're Family - and It Pays to Be Family! Refer your friends and family to Holloway Roofing today!