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Trusted In The Winchester Area Since 1951

New Roof Installation in Winchester, VA

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More than Roofing.

New Roof Installation

A new roof installation is a critical investment in your home’s protection and value. Our team ensures precise installation using quality materials, proper ventilation, and proven techniques to deliver a roofing system built to last for years to come.
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New Construction and Full Roof Installs

A new roof installation sets the tone for decades of protection-so it has to be done right from day one. Whether you’re building new, adding an addition, or replacing a roof down to the decking, the installation must account for structure, ventilation, drainage, and long-term durability. Gregory’s Roofing of Winchester installs roofing systems that meet manufacturer requirements and real-world weather demands in Winchester, VA. We coordinate the right materials, correct underlayment, and precise flashing so the roof performs as a complete unit. A “new roof” that’s missing key details is just an expensive future leak. We focus on doing it once, correctly.

Choosing the Right Roofing System

The best roofing system depends on your home’s style, budget, and performance goals. Asphalt shingles are a popular choice for affordability and design variety; metal roofing can offer exceptional longevity and durability. We help you choose based on roof pitch, exposure, shading, and how long you plan to stay in the home. Gregory’s Roofing of Winchester will explain trade-offs clearly-no overselling, no confusing spec talk. We also ensure accessory components match the selected system, because mixing low-grade flashing or ventilation with premium materials undermines the whole job. If you’re investing in a new roof, the system should be balanced from top to bottom.

What our customers say.

Homeowners across Winchester and the surrounding areas trust Gregory’s Roofing for honest pricing, dependable service, and high-quality results. Our reputation is built on decades of satisfied customers and long-lasting work.
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Find your service

Roof Replacement

Roof Repair

Asphalt Shingle Roofing

Metal Roofing

Residential Roofing

New Roof Installation

Gutter Installation

Window Replacement

Siding Installation

Deck Installation

Screened Porch Install

Patio Cover Installation

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    Get your free estimate.

    Request a no-obligation estimate from our experienced team and get honest guidance tailored to your home and budget.

    Whether you’re planning a roof replacement, exterior upgrade, or minor repair, Gregory’s Roofing of Winchester provides clear communication, fair pricing, and dependable timelines from start to finish.

    A Family Business Built on Trust

    Gregory’s Roofing of Winchester is a locally owned, family-operated company committed to serving our community with integrity. Since 1951, we’ve built lasting relationships by doing the job right and standing behind our work.
    About Us

    FAQs

    How long has Gregory’s Roofing of Winchester been in business?
    We have proudly served the Winchester area since 1951, providing trusted roofing and exterior services backed by decades of experience.
    Do you offer free estimates?
    Yes, we provide free, no-obligation estimates for all roofing and exterior projects.
    What areas do you serve?
    We serve Winchester and surrounding communities throughout the region—contact us to confirm service availability in your area.
    What types of roofing do you install and repair?
    We specialize in asphalt shingle roofing, metal roofing, roof repairs, full roof replacements, and new roof installations for residential homes.
    How do I know if my roof needs repair or replacement?
    If your roof is leaking, missing shingles, showing signs of age, or has sustained storm damage, our team can inspect it and recommend the most cost-effective solution.
    Are your installers licensed and insured?
    Yes, our crews are fully licensed, insured, and trained to meet industry standards and safety requirements.
    What warranties do you offer?
    We stand behind our workmanship and offer manufacturer warranties on materials, with warranty details provided at the time of your estimate.
    Do you offer services beyond roofing?
    Yes, in addition to roofing, we provide gutter installation, siding installation, window replacement, deck installation, screened-in porches, and patio covers.
    How long does a roof replacement take?
    Most residential roof replacements are completed in one day, depending on the size and complexity of the project.