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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

Winchester Roof Installation

Protect Your Property With A New Roof

If you are starting to see leaks, missing shingles, or dark stains on your ceilings, it may be time to plan for a new roof. A properly installed roof is one of the most important systems protecting your home or business, and delaying repairs can allow small issues to turn into costly damage. Our team at Holloway Roofing provides professional Winchester roof installation for residential and commercial properties throughout the Shenandoah Valley.

We understand that installing a new roof is a significant investment, and you want to be confident you are choosing the right materials and the right contractor. Our goal is to give you clear information, straightforward recommendations, and workmanship that is built for Virginia weather. As a locally owned roofing company based in Harrisonburg, we are familiar with how roofs in this region perform through heavy rain, snow, and summer heat.

When you contact us, you are working with a fully licensed and insured Class A contractor that focuses on long-term protection and structural integrity. We offer free, detailed estimates so you can review options, compare costs, and move forward with your roof installation decision with confidence.

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

Why Choose Our Roof Installers

When you plan a roof install Winchester property owners have many contractors to consider, and it can be difficult to see what truly sets one apart from another. We work to make that decision easier by backing our work with national-level credentials and local accountability. Every roof we install is handled by a trained crew that follows manufacturer guidelines from start to finish.

Holloway Roofing is certified as a GAF Master Elite Contractor, a distinction held by a small percentage of roofing companies nationwide. This status allows us to offer the GAF Golden Pledge Warranty, which can provide up to 50 years of material coverage and 25 years of workmanship coverage when we install qualifying systems. For you, that means added confidence that both the products and the installation have strong support behind them.

We are also a CertainTeed SELECT ShingleMaster, which reflects advanced training in installing leading asphalt shingle systems. Combined with our Virginia Class A Contractor’s License and full insurance, these credentials help reduce risk for homeowners and business owners who choose us as their roof installer Winchester. In addition, we maintain an A+ rating with the Better Business Bureau, which reflects our focus on communication, service integrity, and resolving issues if they arise.

Because we are a family-owned company serving the Shenandoah Valley, our reputation in the community matters to us. We have been recognized as one of the region’s top roofing companies, and many of our projects come from repeat customers and referrals. When you trust us with your roof installation, you are working with a local team that expects to see you at the store, at school events, and around town, and we treat your property with that in mind.

Our New Roof Installation Process

Understanding how the installation process works can make planning a new roof feel much more manageable. We follow a clear approach that is designed to protect your property, keep you informed, and deliver a finished roof that performs the way it should. From the first visit to the final cleanup, our team focuses on quality and communication.

Every project starts with a detailed roof inspection. We look at the overall condition of your shingles or other roofing materials, check flashing and penetrations, and evaluate the decking and ventilation as much as can be seen without removing materials. This helps us determine whether a full replacement is the right solution and what specific work will be needed on your Winchester roof installation.

After the inspection, we prepare a free, written estimate that outlines the recommended scope of work, material options, and pricing. We review this with you, answer questions, and help you compare shingles, metal panels, or membrane systems based on appearance, performance, and budget. Our goal is to give you enough information to choose what fits your property best without pressure.

Before work begins, we schedule installation dates that fit as well as possible with your calendar and expected weather conditions. On installation day, our crews arrive on time, set up safety equipment, and protect landscaping, walkways, and other features around your home or business. We typically remove the old roofing down to the decking so we can check for hidden damage and make any necessary repairs before installing new underlayment, flashing, and ventilation components.

Once the roof deck is sound, we install the new roofing system according to manufacturer guidelines. This usually includes ice and water protection in vulnerable areas, high-quality underlayment, drip edge, and properly integrated flashings. Shingles, metal panels, or membrane materials are then installed carefully so water sheds correctly and the roof looks uniform across every slope. Throughout the project, a supervisor is available to address any questions you may have about progress.

Cleanup is a critical part of every job we do. Our crews pick up debris, load removed materials into trailers, and perform a magnetic sweep to collect nails around the property. Before we consider the project complete, we walk the site with you when possible, review what was done, and go over warranty information. We want you to feel comfortable with your new roof and how to contact us if you ever have concerns.

Roof Options For Winchester Properties

Different properties in the Winchester area call for different roofing materials, and we help you match your new system to your goals. We install a range of products for steep-slope and low-slope roofs and can explain how each option responds to local weather conditions. Our team focuses on combining appearance, performance, and value for every new roof Winchester owners choose.

Asphalt shingles remain one of the most common choices for homes. Architectural or dimensional shingles provide a layered look and can offer strong wind resistance when installed correctly. With our GAF and CertainTeed certifications, we are able to recommend shingle lines that have proven reliable in four-season climates and that qualify for enhanced warranty coverage when we install them according to program requirements.

Metal roofing is another option that can make sense for certain homes and light commercial buildings in the Shenandoah Valley. Properly installed metal panels can offer excellent durability and shed snow and rain efficiently. We discuss considerations such as noise, appearance, and cost so you can decide if metal is a good fit for your property or if high-quality shingles might be the better choice.

For commercial buildings, additions, or sections of a home with low-slope or flat areas, we install membrane systems designed for that application. These systems are built to move water toward drains or gutters and can provide a durable surface when paired with the right insulation and flashing details. When we review options with you, we explain how these materials work and what maintenance they typically require over time.

No matter which material you select, we focus on details that are especially important in this part of Virginia, such as ventilation, ice protection at eaves, and flashing transitions where roofs meet walls or chimneys. Proper attention to these areas can help reduce the risk of leaks during heavy rain or snowmelt and contribute to the overall life of your new roof.

When A New Roof Makes Sense

One of the most common questions we hear is whether a roof truly needs to be replaced or if a repair is still a reasonable option. We understand that you want to avoid unnecessary expense, and we approach each inspection with that in mind. During our assessment, we look at the entire system, not just the most obvious problem area.

There are several signs that often indicate a roof is nearing the end of its useful life. These can include widespread shingle curling or cracking, significant granule loss that exposes bare asphalt, sagging areas on the roof plane, or repeated leaks in different locations. When these conditions are present, continued patching can become less effective and more costly over time compared to a properly planned roof installation.

Storm damage is another factor that can lead to a full replacement. Strong winds in the region can lift or remove shingles, and hail can bruise or fracture shingle mats in ways that are not always obvious from the ground. When damage is more than cosmetic, it can shorten the life of the roof and reduce its ability to protect the structure. During our inspections, we document what we see so you can review conditions yourself.

In situations where weather events are involved, property owners often need to work with their insurance company. Our team provides inspections and documentation to help you understand what may be covered under your policy. While coverage decisions are made by your insurer, we can assist by outlining the scope of work required to restore the roof and by answering questions about the installation process.

There are also times when owners choose to replace a roof proactively. For example, you may be preparing to sell or refinance and want a roof that will not raise concerns during buyer inspections or appraisals. In these cases, we discuss your timeline and goals, then recommend a roof installation approach that supports the long-term value of the property.

Schedule Your Roof Installation Estimate

When you are ready to explore your options for roof install Winchester property owners can start with a free, no-obligation estimate from our team. We will inspect your roof, explain what we find in straightforward terms, and provide a clear proposal that outlines recommended work, material choices, and pricing. You will know exactly what is included before you make any decisions.

By choosing Holloway Roofing, you are working with a credentialed roofing company that installs systems backed by strong manufacturer and workmanship warranties. We take care to protect your property, communicate during the project, and leave your home or business clean when the work is complete. Our team is local, so if questions come up later, you know how to reach us.

We invite you to contact us to schedule an on-site visit at a time that works for you. Our goal is to make planning a new roof as simple and predictable as possible so you can focus on enjoying a dry, secure property.

Call (540) 924-1553 to schedule your free roof installation estimate today.

Frequently Asked Questions

How do I know I need a new roof?

You may need a new roof if you see widespread shingle damage, recurring leaks, or sagging areas. During our inspection, we look at the whole system and explain whether repair or replacement is the better long-term option. Our goal is to help you avoid unnecessary costs.

How long will my roof installation take?

Most residential roof installations are completed within one to a few days, depending on size, complexity, and weather. We outline the expected schedule before work begins and keep you updated if conditions affect timing. Our crews work efficiently while maintaining quality and safety.

What warranties do you offer on new roofs?

We offer manufacturer warranties and workmanship coverage on new installations. As a GAF Master Elite Contractor, we can provide access to the GAF Golden Pledge Warranty on qualifying systems, which adds strong long-term protection. During your estimate, we explain available warranty options in detail.

Will your team protect and clean up my yard?

Yes, protecting and cleaning your property is a standard part of our process. We use tarps and other methods to shield landscaping and walkways, then remove debris and perform a magnetic nail sweep at the end of the job. We work to leave your yard tidy.

Can you help if my roof damage involves insurance?

We regularly assist property owners whose roofs have storm or wind damage. Our team documents conditions, explains what repairs or replacement are needed, and can share that information with you for your insurance claim. While we do not control coverage decisions, we help you understand the roofing scope.

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!