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Trusted In The Winchester Area Since 1951

Roof Repair in Winchester, VA

More than Roofing.

Roof Repair

From small leaks to storm damage, our roof repair services restore the safety and performance of your roof quickly and effectively. Gregory’s Roofing of Winchester identifies the source of the problem and delivers lasting repairs that prevent further damage and costly future issues.

Common Roof Problems We Fix

Roof issues rarely improve on their own-most get worse quietly. The frequent culprits we see in Winchester include missing or damaged shingles from wind, nail pops, cracked pipe boots, failing flashing around chimneys or walls, and leaks caused by poor ventilation or aging underlayment. Water can travel far from the entry point, so the stain you see indoors is not always where the roof is failing. Gregory’s Roofing of Winchester approaches repairs like diagnostics, not guesses: we identify the source, assess surrounding weak points, and recommend the repair that actually solves the problem. If a repair is the right answer, we’ll do it. If the roof is at the end of its life, we’ll say so-because “temporary fixes forever” is how homeowners waste money.


Leak Detection Without the Runaround

The worst roof repair experiences come from vague explanations and repeat callbacks. Our process focuses on certainty: inspection, documentation, and a repair plan tied to the real failure points-shingles, flashing, penetrations, valleys, or decking. We check the attic when appropriate, evaluate ventilation and moisture patterns, and look for installation defects that cause recurring leaks. In Winchester, wind-driven rain can exploit tiny weaknesses, so we look beyond the obvious. Gregory’s Roofing of Winchester explains what we found in plain language, shows you the problem areas when possible, and outlines next steps. The goal is simple: stop the leak, prevent re-entry, and keep the roof system functioning. You shouldn’t have to “try a repair” multiple times just to get results.

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.

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.

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.