Skip to main content

|

Trusted In The Winchester Area Since 1951

Siding Installation in Winchester, VA

Get In Touch With A Roofing Expert Now

More than Roofing.

Siding Installation

New siding not only improves the appearance of your home but also adds an important layer of protection. Gregory’s Roofing of Winchester installs durable siding options that resist weather damage while increasing energy efficiency and long-term value.
Get your free quote.

What Quality Siding Does for Your Home

Siding is your home’s protective shell-it impacts curb appeal, moisture control, and long-term maintenance. In Winchester, siding needs to handle rain, wind, humidity, and temperature swings without warping or leaking. Quality siding installation helps keep water out of the wall system, protects insulation performance, and reduces repainting or repair cycles. Gregory’s Roofing of Winchester installs siding with attention to weather-resistive barriers, flashing, and clean transitions around windows, doors, and corners. If your current siding is cracked, rotting, or constantly peeling paint, it’s not just an appearance problem-it’s a protection problem.

Siding Options and How to Choose

Different siding materials serve different priorities: durability, maintenance, and style. Many homeowners want something that looks great but doesn’t require constant upkeep. The best choice depends on your home’s design, exposure, and budget. Gregory’s Roofing of Winchester will help you evaluate options realistically-what holds up, what fades, what needs maintenance, and what delivers value. We also consider how siding pairs with your rooflines, trim, and gutters so the exterior looks cohesive. Avoid choosing based on price alone; cheap siding with weak installation often leads to moisture issues and replacement sooner than expected.

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.
More Reviews

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

View Gallery

    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.