Trusted In The Winchester Area Since 1951
Window Replacement in Winchester, VA
More than Roofing.
Window Replacement
Upgrading your windows improves energy efficiency, comfort, and curb appeal. Our window replacement services provide homeowners with modern, high-quality windows that reduce drafts, lower energy costs, and enhance the overall look of their home.
How New Windows Improve Comfort and Efficiency
Old windows can quietly drain comfort and money-drafts, temperature swings, and condensation are common signs. New windows can improve insulation, reduce air leakage, and help your HVAC system work less. In Winchester, seasonal changes make window performance matter: summer heat gain and winter drafts both hit your utility bills. Gregory’s Roofing of Winchester approaches window replacement with a focus on proper fit and sealing, because even the best window performs poorly if installed incorrectly. We help you choose options that match your goals-energy efficiency, noise reduction, and appearance-without upselling you into features you don’t need.
Common Signs It’s Time to Replace
If your windows are hard to open, foggy between panes, visibly rotting, or letting in noticeable drafts, replacement is often smarter than patching. Condensation between panes usually indicates seal failure, meaning the window has lost much of its insulating value. Water intrusion around frames can lead to hidden damage in walls and trim. Gregory’s Roofing of Winchester can inspect your existing windows and identify whether the issue is the unit itself or surrounding trim/flashing. The goal is to stop air and water problems at the source. If you’re repeatedly painting, caulking, and still dealing with drafts, you’re not maintaining-you’re losing ground.
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.