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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

Shingle Roofer in Winchester

Protect Your Property With Trusted Shingle Roofing

If you have noticed missing shingles, leaks, or dark stains on your ceilings, you know your roof needs attention. You want a dependable shingle roofing team that will give you clear answers and a long-lasting solution, not a quick patch that fails at the next storm.

At Holloway Roofing, we provide asphalt shingle roofing for homes and commercial properties in and around Winchester. Our team combines manufacturer training, strong warranties, and careful workmanship so your roof can stand up to Virginia’s changing seasons. We start with an honest assessment, then walk you through options that fit your property and budget.

We are a GAF Master Elite Contractor and CertainTeed SELECT ShingleMaster. These credentials, along with our Class A Contractor’s License in Virginia and full insurance, mean your shingle roof is installed to high standards and backed by proven manufacturers. If you are ready to have your roof evaluated, call (540) 924-1553 to schedule a shingle roof inspection.

Why Choose Our Shingle Roofing

When you compare roofing companies, the biggest questions are usually about quality and trust. You want to know that the crew on your roof is properly trained, that your money is well spent, and that your roof will be protected for years. We build our shingle roofing approach around those concerns.

As a GAF Master Elite Contractor, we are part of a small group of roofing companies nationwide that meet strict requirements for training, installation practices, and customer satisfaction. This status allows us to offer the GAF Golden Pledge Warranty, which provides up to 50 years of material coverage and up to 25 years of workmanship coverage on qualifying shingle roofs. We are also a CertainTeed SELECT ShingleMaster, which reflects our knowledge of leading asphalt shingle systems from another highly regarded manufacturer.

Our Class A Contractor’s License in Virginia and full insurance coverage help protect you from risk on your property. You are not relying on a casual crew, you are working with a licensed contractor that follows state requirements and manufacturer guidelines. We also maintain an A+ Rating with the Better Business Bureau, and we have received national recognition through the GAF President’s Club Award along with regional honors such as being voted a top roofer in the Shenandoah Valley.

Because we are a family-owned company based in the valley, we understand how roofs here are affected by winter snow, heavy rain, and summer heat. Our goal is not just to install shingles, but to recommend systems that match local conditions and the specific needs of your home or business. From the first inspection to the final cleanup, we focus on clear communication, punctual scheduling, and leaving your property clean and safe when we are finished.

Shingle Roofing Services We Provide

Every roof and every property owner’s situation is different. Some roofs only need targeted shingle repairs, while others are at the end of their life and require full replacement. We take time to understand what is happening on your roof so we can recommend the most sensible path forward.

We work on both residential and commercial properties that use asphalt shingles, including steep-slope roofs commonly found on single-family homes, duplexes, and smaller commercial buildings. If you are dealing with a leak, we start by tracing the source, checking the surrounding shingles, flashing, and roof penetrations. For storm damage, we document what we find and can assist you as you work through an insurance claim, helping you understand what is typically covered and what your options may be.

When a roof is nearing the end of its useful life, we discuss shingle roof replacement in plain language. We explain your choices in shingle styles and colors from manufacturers like GAF and CertainTeed, and how upgraded components, such as underlayments and ventilation, can support a longer-lasting system. For properties in this part of the Shenandoah Valley where roofs see a wide range of temperatures, we consider both appearance and performance when recommending materials.

Our shingle roofing services include:

  • Shingle roof inspections and condition assessments
  • Leak detection and targeted shingle repairs
  • Complete shingle roof replacement for homes
  • Shingle roofing solutions for small commercial properties
  • Storm damage evaluations and insurance claim support
  • Ongoing maintenance to help extend roof life

In every case, we provide a free, written estimate that outlines the scope of work, materials, and approximate timing. We review this with you so you can ask questions and feel confident before you approve anything. Our recommendations are based on what will best protect your property, not on selling the largest possible project.

 

Our Shingle Roofing Process

Many property owners hesitate to call a roofer because they are unsure what will happen next. We structure our process so you always know what we are doing and why. This helps you plan around your schedule and feel comfortable with each step.

It starts when you contact our team to request an inspection for your roof in or around Winchester. We schedule a visit at a convenient time and arrive ready to evaluate the entire roofing system, not just the most obvious problem area. During the inspection, we look at shingles, flashing, penetrations, gutters, and attic ventilation. We often take photos so we can show you exactly what we are seeing.

After the inspection, we sit down with you, either in person or by phone, and explain our findings in clear terms. If we believe repair is a good option, we describe what that would involve and how long it is likely to last. If we recommend replacement, we explain why, and we outline available shingle products, color choices, and warranty options that fit your property. Our written estimate includes labor, materials, and any related work such as decking repairs if those are anticipated.

Once you approve the work, we schedule your project and explain what to expect on installation day. Our crews arrive on time, protect landscaping and walkways where practical, and work efficiently while keeping the site as organized as possible. During the job, a supervisor is available to answer questions and update you on progress. At the end, we complete a detailed cleanup that includes picking up debris and using magnets to collect loose nails where appropriate, then we walk the project with you so you can see the finished result.

Shingle Roofs In Local Conditions

Roofs in Winchester and across the Shenandoah Valley face a mix of weather conditions that can be tough on asphalt shingles. Winter snow and ice can stress older roofs, spring and summer storms can lift or tear shingles, and high summer temperatures can speed up aging on weaker materials.

On many homes here, we see issues such as shingles that have lost granules, lifted shingles at the roof edges, cracked sealant at flashing, or wear around vents and chimneys. Sometimes these problems show up inside first as stains on ceilings, peeling paint near the ceiling line, or musty odors from moisture. Catching these early can make the difference between a simple repair and more significant structural work.

When we design a shingle roofing solution for a property in Winchester, we consider how these conditions will affect the roof over time. That is why we work with high-quality, warrantied materials from manufacturers like GAF and CertainTeed, and why we follow their installation guidelines closely. Proper underlayments, ice and water protection in critical areas, and appropriate ventilation all help your roof handle the local climate more effectively.

Common signs you should schedule a shingle roof inspection:

  • Missing, curled, or cracked shingles visible from the ground
  • Shingle granules collecting in gutters or at downspouts
  • Water stains or spots on ceilings or upper walls
  • Areas of the roof that look uneven, sagging, or dark
  • Recent wind or hail storm in your neighborhood

If you notice any of these on your property, it is a good idea to have our team take a closer look. We can help you understand whether a repair is likely to solve the issue or whether it may be time to start planning for a larger project.

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We Always Strive for Five Stars!

Check Out Our Reviews
    “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!