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This video shows the team, office building, roof replacement process, and the new roof, no mess technology for Holloway Roofing.

Protecting what matters Most High-Quality, Innovative Roofing Solutions for Your Home or Business

Why compromise? Choose Holloway Roofing and experience The Holloway Difference!

At Holloway Roofing, We Guarantee...

  • Free Roof Inspection & Consultation
    One-on-one roofing consultation with our roofing experts, for FREE!
  • Review, Revise & Finalize Project Agreements

    We make financing projects and insurable loss claims a breeze!

  • Schedule & Deliver Your Roofing Project

    Work is always scheduled on a first-come, first-serve basis. Upon contract closure, your production date will be secured!

Need Service Outside of Harrisonburg? We've Got You Covered! Call (540) 924-1553 to Make an Appointment!
  • Afton
  • Arrington
  • Augusta County
  • Augusta Springs
  • Barboursville
  • Bridgewater
  • Broadway
  • Buena Vista
  • Bumpass
  • Charlottesville
  • Churchville
  • Craigsville
  • Crimora
  • Crozet
  • Dayton
  • Deerfield
  • Earlysville
  • Edinburg
  • Elkton
  • Fairfield
  • Fishersville
  • Fork Union
  • Fort Valley
  • Free Union
  • Fulks Run
  • Gladstone
  • Gordonsville
  • Goshen
  • Greenville
  • Greenwood
  • Grottoes
  • Harrisonburg
  • Hinton
  • Hot Springs
  • Ivy
  • Keezletown
  • Lexington
  • Linville
  • Louisa
  • Luray
  • Lyndhurst
  • McGaheysville
  • Middlebrook
  • Middletown
  • Mount Crawford
  • Mount Jackson
  • Mount Sidney
  • Mount Solon
  • Nellysford
  • New Market
  • North Garden
  • Orange
  • Palmyra
  • Penn Laird
  • Port Republic
  • Quicksburg
  • Rhoadesville
  • Rockingham County
  • Ruckersville
  • Scottsville
  • Shenandoah
  • Shipman
  • Singers Glen
  • Somerset
  • Stanardsville
  • Stanley
  • Staunton
  • Staunton
  • Steeles Tavern
  • Stephens City
  • Stephens City
  • Strasburg
  • Stuarts Draft
  • Swoope
  • Swoope
  • Timberville
  • Toms Brook
  • Troy
  • Unionville
  • Verona
  • Waynesboro
  • West Augusta
  • Weyers Cave
  • Winchester
  • Woodstock

Gutter Services in Charlottesville

Strong, well-maintained gutters play a key role in protecting homes and businesses across Charlottesville from water damage. At Holloway Roofing, our licensed and insured team provides clear communication, proven results, and quality craftsmanship on every gutter installation, repair, and cleaning project. As a GAF Master Elite Contractor and President’s Club Award recipient, we bring nationally recognized standards to every local property we serve.

Gutters do more than carry rainwater away. They help prevent basement leaks, foundation cracks, and soil erosion—problems that often affect properties in Charlottesville’s climate and tree-heavy neighborhoods. Seasonal storms and falling leaves make regular care especially important. Our team considers your landscape, roof design, and any historic district guidelines before recommending solutions that match both performance and curb appeal.

Need gutter service in Charlottesville? Call Holloway Roofing at (540) 924-1553 or send us a message online today.

Why Choose Us for Gutter Service in Charlottesville?

We believe quality gutter service should be easy, dependable, and tailored to your needs. With Holloway Roofing, you get a stress-free process from your first call, starting with free inspections and detailed estimates with no hidden costs. Our team stays up to date on industry innovations, uses top-grade materials, and offers prompt, same-day solutions whenever possible so your property stays protected—no matter the weather.

  • Recognized Excellence: Awarded GAF President’s Club honor and voted regional best—demonstrates consistent, top-level service.
  • Fully Insured Peace of Mind: We maintain comprehensive insurance and required licensing for every job.
  • Stress-Free Process: From free inspections and fast turnaround to clear communication and financing options, we make gutter care simple and efficient.
  • Premium Materials & Craftsmanship: We use proven installation methods for long-lasting gutter systems.
  • Proven Local Results: Our solutions are crafted specifically for Charlottesville and the surrounding climate, ensuring optimal, year-round protection.

Our reputation for transparency and upfront pricing means you always know what to expect—no last-minute surprises or upsells. By choosing a company committed to integrity and professionalism, you gain a partner who prioritizes clear communication and practical, long-lasting results. Whether you need urgent gutter repair after a storm, a proactive maintenance plan, or new gutter installation in a historic area, our team brings hands-on experience and deep local knowledge to every service. We are proud to provide gutter service in Charlottesville that not only solves immediate issues but also protects your property for years to come.

Because we also work extensively with roofing, siding, and fascia, we understand how each part of your exterior works together and how the right gutter company in Charlottesville can help preserve the entire building envelope. This broader perspective allows us to recommend solutions that protect your roof edges, prevent premature wood rot, and reduce the chances of water intrusion behind walls. When we suggest upgrades or repairs, we explain the tradeoffs in cost, maintenance, and long-term protection so you can choose what works best for your budget and plans for the property.

Comprehensive Gutter Services for Homes & Businesses in Charlottesville

Our team offers a full suite of gutter services for both residential and commercial properties throughout Charlottesville and Albemarle County. Every service begins with a detailed assessment, followed by personalized recommendations that fit your property’s architecture, landscape, and local code requirements, so you get the right solution every time.

  • Gutter Installation: Seamless gutters custom fit to your home or business, offering lasting durability and enhanced curb appeal.
  • Gutter Repair: Fast, effective solutions for leaks, sagging, or storm damage using only high-quality materials.
  • Gutter Cleaning & Maintenance: Routine cleaning and inspections to keep water flowing, even during heavy rains or after the leaves fall in autumn.
  • Downspout Solutions: Repair and install downspouts to make sure water is directed away from your foundation and landscaping, reducing erosion and moisture risks.
  • Leaf Guard & Protection Systems: Quality protection systems that minimize debris buildup and prevent clogs, ideal for Charlottesville’s treed neighborhoods.

For commercial properties, we understand that gutter problems can disrupt operations, pose slip hazards, and lead to expensive structural repairs if ignored. We work with property managers, HOAs, and business owners to plan work around operating hours, secure appropriate access, and coordinate with other trades when needed. Our team is familiar with the demands of flat and low-slope roofs commonly found on offices, churches, and retail buildings in the area, and we design drainage solutions that move water efficiently away from critical entryways, sidewalks, and parking areas.

Homeowners in Charlottesville and surrounding communities also turn to us when updating other parts of their exterior, such as roofing, siding, or decks. Coordinating gutter service with these projects can reduce labor overlap, minimize disruption to your household, and create a more cohesive finished look. We can match or complement existing trim colors, discuss options like oversized downspouts for steep roofs, and plan for future additions such as patios or walkways so that your current investment continues to perform well as your property evolves.

Our Process: Gutter Installation, Repair & Maintenance Made Simple

Customer experience is at the heart of everything we do. From your first call to project completion, our process is designed to take the stress out of gutter service in Charlottesville while keeping you informed at every stage.

  • Free Inspection & Assessment: We conduct a thorough on-site inspection, evaluating your gutter system’s condition, identifying blockages, improper pitch, or worn areas, and providing straightforward feedback on necessary repairs or upgrades.
  • No-Obligation Estimate: We prepare a clear, itemized quote outlining recommended options, so you are never left guessing. Flexible financing is available for larger projects to fit your needs and budget.
  • Scheduling & Preparation: Once you approve the plan, we schedule the work at your convenience, often offering same- or next-day service for emergencies so your property is protected quickly.
  • Professional Service: Our respectful team works efficiently, uses advanced tools and materials, and takes care to protect your landscaping and neighboring properties. We observe local HOA guidelines and keep a tidy work area at all times.
  • Final Walk-Through & Maintenance Tips: After installation or repair, we walk you through the finished project, answer questions, and share tips for ongoing gutter care. We are always just a call away for future service or advice.

During the inspection phase, we may also review how your gutters tie into broader site drainage, such as French drains, splash blocks, or underground piping. In parts of Charlottesville where lots sit on slopes or near creeks, directing water to the right place can make a noticeable difference in how often you see pooling or damp spots. When appropriate, we discuss options like extending downspouts, adjusting discharge locations, or coordinating with other contractors so your entire drainage plan works as a unified system.

Throughout the project, our goal is to minimize disruption to your daily routine while maintaining open communication, which is one reason many homeowners call us when they are searching for a dependable gutter company in Charlottesville. We provide clear start and finish times, update you on weather-related adjustments, and review any unexpected findings before moving forward. At the end of the job, we confirm that your gutters are flowing properly, ensure that debris has been removed from the property, and leave you with practical, easy-to-follow guidance for seasonal care so you can get the most from your investment.

Choosing the Right Gutter System for Your Property

Selecting the best gutter system for your home or building is not just about appearance; it affects how well your property handles the kind of rain, snow, and leaf buildup common in Central Virginia. We help you compare options based on roof pitch, fascia condition, tree coverage, and how water naturally moves across your lot. By walking you through the pros and cons of different materials and profiles, we make it easier to choose a setup that will perform well for many seasons without constant attention.

Many residential properties in Charlottesville benefit from seamless aluminum gutters, which offer a balance of affordability, durability, and low maintenance. For homes with more visible rooflines or historic architectural details, we can discuss options like half-round profiles, decorative hangers, or color selections that coordinate with trim and shutters. On larger or steeper roofs, we may recommend oversized gutters or downspouts to better handle intense summer storms, reducing the risk of overflow in areas where landscaping or hardscaping is close to the foundation.

Commercial buildings and multifamily properties often have different needs, especially when they include long roof runs, parapet walls, or flat sections that collect water. In these situations, we evaluate whether box gutters, scuppers, or additional drains are needed to move water efficiently and comply with local building practices in Charlottesville and Albemarle County. We also consider how maintenance access, snow shedding, and nearby pedestrian areas might influence the best configuration so your investment supports safety as well as appearance.

Preventing Water Damage With Proactive Gutter Care

Proactive gutter maintenance is one of the most cost-effective ways to prevent water damage to your home or business. Rather than waiting for leaks to show up inside, we encourage property owners to think about how their gutters perform during heavy downpours, wind-driven rain, and freeze-thaw events that are common in this part of Virginia. By planning regular service, you can catch minor issues before they turn into larger problems that affect foundations, basements, and finished living spaces.

During a typical maintenance visit, we focus on more than just clearing out leaves and debris. We also look for early signs of trouble such as loose fasteners, seam separation, worn sealant at corners, and areas where water is bypassing the system altogether. In Charlottesville’s hilly neighborhoods and older subdivisions with mature trees, staying ahead of these concerns can help protect retaining walls, walkways, and driveway edges from erosion and settlement caused by uncontrolled runoff.

For owners who prefer a more hands-off approach, we can discuss setting up a recurring service schedule that aligns with the local seasons, such as early spring after winter storms and late fall after peak leaf drop. This kind of planned gutter service helps you avoid emergency calls after a major storm and gives you predictable upkeep that fits into your annual property budget. When we see patterns—like a particular corner that clogs every year or an area where ice dams tend to form—we share practical suggestions and improvements so your system can better handle Charlottesville’s changing weather over time.

Frequently Asked Questions

How Often Should I Schedule Gutter Cleaning in Charlottesville?

Twice a year—typically in spring and fall—is generally recommended, but homes near dense trees or with rooflines prone to debris may benefit from additional cleanings to prevent clogs and water damage.

What Are the Signs My Gutters Need Repair or Replacement?

Look for sagging, rust, leaks, peeling paint, or water pooling near your foundation. Addressing these issues early can help you avoid more serious and costly damage over time.

Can Gutter Installation Be Done Year-Round in Charlottesville?

Yes, gutter installation can be performed in most seasons, weather permitting. Our team adapts to Virginia’s varying climate and schedules work for optimal conditions and minimal disruption.

Are There Local Regulations Affecting Gutter Work in Charlottesville?

Most gutter work does not require a permit, but properties in historic districts or under an HOA may need to follow additional review processes. We guide you through all necessary steps for compliance.

Do You Offer Warranties on Gutter Services?

All new installations come with premium manufacturer warranties, in addition to our own craftsmanship guarantee. Specific terms are always clearly outlined in your estimate and contract.

Contact Us for Reliable Gutter Service in Charlottesville

If you want reliable, professional gutter service in Charlottesville, reach out to Holloway Roofing today. Our friendly, knowledgeable team is available to answer your questions, schedule a complimentary inspection, and provide a clear, no-obligation estimate so you can make a confident decision without stress or surprises. Our commitment to quality, efficiency, and honest advice ensures a smooth experience from start to finish. Let us take the worry out of home or business maintenance—call (540) 924-1553 and discover the dedication that sets us apart in Charlottesville.

When you contact us, we take the time to understand whether you are dealing with an active leak, a long-term drainage concern, or planning ahead for a renovation. From there, we help you decide which gutter service will make the most impact for your home or building today, while also considering how Charlottesville’s heavy rains and leafy seasons may affect your property in the future. By pairing practical recommendations with clear pricing and timelines, we make it easier to move forward with the right level of work instead of putting off needed improvements.

We Always Strive for Five Stars!

Check Out Our Reviews

At Holloway Roofing, your satisfaction is our priority! See for yourself what our customers have to say about working with us.

    “Great Experience!”
    “They did an outstanding job and you could tell they take pride in their work.”
    - Kayla S.
    “Highly Recommend!”
    “Hard-working guys and didn't cut corners. Will be using them for other projects in the future.”
    - Foster K.
    “Best in the Valley!”
    “Great work and excellent customer service!”
    - Emilee L.
Experience the Holloway Difference! "We made a promise as a team to always stay up to speed with all of the latest measures of technology, materials, & equipment to ensure the safety of our customers and employees."

- James Holloway, Owner

Get Peace of Mind

Contact Your Local Roofing Experts Today!

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Our Credentials

Backed by Industry-Leading Certifications
  • BBB A+
  • GAF Master Elite
  • Over 10 Years Service
  • Catch-All Roofing System
  • Velux Certified Installer
  • New Roof, No Mess
  • GAF Presidents Club
  • Top Rated local roofing contractor
  • SVB
  • harrisonburg chamber of commerce
  • american owned
  • triple
  • trust
  • financing
  • top rated
  • We Offer Financing! Helping You Get the Roof You Deserve

    A new roof is a big investment! That's why we provide a variety of financing options to help make the buying process easier.

  • The Holloway Difference Don't Do It Their Way, Do it Holloway!
    At Holloway Roofing, our workmanship, materials, professionalism, equipment, warranties, training, and certifications set us apart from the rest!
  • New Roof, No Mess®! Keeping Your Property Safe
    THE EQUIPTER RB4000 is a state-of-the-art roofing debris containment system that is designed to help protect what matters most.
  • Referral Rewards Earn Up To $100 with Each New Referral!

    Once You Do Business with Us, You're Family - and It Pays to Be Family! Refer your friends and family to Holloway Roofing today!