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Trusted In The Winchester Area Since 1951

Winchester’s #1 Roofers!

For over 70 years, Gregory’s Roofing of Winchester has delivered dependable roofing and exterior solutions backed by craftsmanship, integrity, and unmatched local experience. From small repairs to full replacements, we protect what matters most.
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More than Roofing.

All-In-One Exterior Services.

Gregory’s Roofing of Winchester offers complete exterior solutions under one roof, saving you time, stress, and money. Whether you need roofing, siding, gutters, windows, or outdoor living upgrades, our experienced team delivers quality results you can trust.
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Quality Craftsmanship Built to Last

Every project we take on is completed using proven materials, skilled workmanship, and attention to detail. We don’t cut corners, we build solutions designed to withstand Winchester’s weather and stand the test of time.

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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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.

    Financing Available