The best-rated roofers serving Winchester, VA, independently researched and ranked on rating, review volume and genuine local reputation.
The best roofers in Winchester, VA are Gregory's Roofing of Winchester, Winchester Roofing, GNS Roofing, Alamo Roofing and Jesus Roofing. Each is an independently researched local operator, ranked on reputation, reviews and genuine local presence, and none paid to appear.
One business can feature above the Top 5 on this page, clearly labeled. A great way for a newer or smaller pro to get seen first.
Established in 1951, Gregory's Roofing of Winchester has protected local homes for over seventy years, making it one of the most established roofers in the area. This locally owned, family-operated firm fits and repairs asphalt shingle and metal roofs and also handles gutters, siding, windows and decking, with fully licensed and insured crews. Homeowners return to it for honest pricing and dependable, high-quality work backed by manufacturer warranties.
Based on S. Braddock Street in the heart of Winchester, this family-owned firm has delivered roofing, siding and window work for around 25 years. It is a Virginia Class A residential building contractor, a BBB A+ accredited business and a CertainTeed Master Craftsman, covering Winchester City plus Frederick, Clarke, Loudoun and Warren counties. Positioning itself as a rooted local neighbour rather than a storm chaser, it holds an excellent Google review reputation built on integrity and craftsmanship.
GNS Roofing is a full-service, family-owned roofing company led by Jose Sobalvarro and based in the White Post area just outside Winchester. The licensed and insured team brings decades of combined experience to shingle, metal and rubber roofs, repairs, chimney flashing and siding across Winchester, Berryville, Strasburg and the West Virginia panhandle. With hundreds of roofs completed and a strong body of positive reviews, it is a solid choice for local homeowners.
Alamo Roofing is a local, family-owned contractor serving Winchester and the surrounding counties with over twenty years of combined experience. The fully licensed and insured team installs and repairs roofs, custom gutters and siding, and holds certified-installer status with IKO, GAF and Owens Corning. It backs its work with a lifetime workmanship warranty and a satisfaction guarantee, suiting homeowners who want manufacturer-certified quality from a local firm.
Jesus Roofing LLC is a locally based roofing contractor operating out of Winchester, focused on residential roof repair and installation. The company emphasises on-time, on-budget work and quality finishes, and reports positive customer feedback across the Winchester area. A straightforward local option for homeowners seeking roof repairs or a full replacement.
The best roofers serving Winchester, VA are based in and around Winchester and White Post. With the Northeast's four seasons and older housing stock to contend with, roofs take a real pounding, so a proven local pro makes all the difference, and we've done the legwork to surface only the operators worth calling.
Gregory's Roofing of Winchester currently tops the list, but every business here earns its place the same way: we research each roofer genuinely operating near Winchester, weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, and rank on merit. No business can pay into this list, the single featured spot above it is the only paid placement, and it's always clearly labeled.
| Business | Best for |
|---|---|
| 1. Gregory's Roofing of Winchester | Winchester & surrounding communities · Roofing & exteriors |
| 2. Winchester Roofing | Winchester, Frederick & Clarke Counties · Roofing, siding & windows |
| 3. GNS Roofing | Winchester & Northern Virginia · Residential roofing |
| 4. Alamo Roofing | Winchester, Frederick & Clarke Counties · Roofing, gutters & siding |
| 5. Jesus Roofing | Winchester, VA · Residential roofing repair & installation |
Our current top picks are Gregory's Roofing of Winchester, Winchester Roofing, GNS Roofing, Alamo Roofing and Jesus Roofing, ranked #1 to #5 on reputation and review volume. This list was last updated July 2026. Every business is independently researched and ranked on merit, never paid placement.
We research every roofer genuinely operating in and around Winchester, then weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, review volume, and a genuine local track record. No business can pay to appear in the ranked Top 5.
No. The ranked Top 5 is editorial and cannot be bought. The only paid option is the single featured spot above the list, which is always clearly labeled as featured.
Start with Gregory's Roofing of Winchester, our current #1 pick, then get written quotes from two or three on this list, read their most recent reviews, and confirm they cover your part of Winchester. A good roofer responds promptly, explains the work clearly, and is upfront about pricing.
We rank on independent reputation and reviews, not licensing checks. Requirements vary by state and trade, so always confirm a pro's current license and insurance directly with them before any work begins.
Not sure what to ask or what a fair process looks like? Read our guide: 5 Signs You Need a New Roof (and 3 That Can Wait).
Own the featured spot above this Top 5, clearly labeled. A great way for a newer or smaller pro to get seen first. $39/month.