4.9
600+ Reviews
WT Anderson Roofing

Expert Chesapeake Roof Installation - GAF Master Elite® Contractors

For decades, WT Anderson has been the go-to certified roofing company for homeowners across Hampton Roads. We deliver unparalleled quality, durable roofing systems, and peace of mind with our expert workmanship warranty.

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Technical visualization of a GAF Master Elite roof installation in Chesapeake, VA. WT Anderson master elite crew performing a full residential reroofing project following VUSBC Chapter 15 high-wind fastening protocols.
GAF President's Club Winner 2025 - WT Anderson
GAF Certified Contactors

Licensed & Insured

Quality Material & Builds

We take pride in the details

Industry Leading Warranty

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Our Comprehensive Roofing and Exterior Services

Verified Field Leadership (LinkedIn Linked)
Jonathan Hill, Chesapeake Project Lead, coordinating with the BHAR for roof material approvals in local historic zones.
Jonathan Hill Chesapeake Project Lead
Héctor Miranda, PM and Drone Specialist, performing a post-installation quality assurance scan on a Chesapeake residential project.
Héctor Miranda PM & Navy Veteran
David Richardson, Exterior Consultant, providing technical roofing material comparisons and cost-benefit analysis for a Chesapeake homeowner.
David Richardson Exterior Consultant

New Roof Installation & Replacement

When it's time for a new roof, you need a team you can trust to do the job right. A complete roof replacement is a critical home improvement project that protects your family and property for decades. We specialize in new roof construction and replacement for homeowners in Chesapeake, VA, and the surrounding Hampton Roads area. Whether your current roof is showing signs of an aging roof, like significant granule loss and curling shingles, or has suffered extensive storm damage, our process begins with a thorough, free roof inspection. Our expert roofers will help you select the best materials for your home and budget, from durable and popular architectural shingles (asphalt shingle roofing) from top brands like GAF, Owens Corning, and CertainTeed, to modern and long-lasting standing seam metal roofing systems. A new roof from WT Anderson not only stops leaks but also enhances curb appeal and can improve your home's energy efficiency, providing a superb return on investment.

⭐⭐⭐⭐⭐ "Highly Competitive & Professionally Detailed — So Glad We Chose Them!" "We had a new roof installed by WT Anderson and they did a great job! We were very impressed with our initial consultation; the inspection was thorough and informative. Their estimate was highly competitive and the contract was professionally written and detailed. The installation went smoothly and we are enjoying our new roof. So glad we chose WT Anderson!"Jang Lee, New Roof Installation

Expert Roof Repair

Even small roof problems can lead to significant water damage if left unaddressed. Our dedicated roof repair team is equipped to handle all types of issues promptly and effectively. We are experts in storm damage repair, whether it's from hail damage that has compromised your shingles or high winds that have caused missing shingles. Our services cover everything from complex roof leak repair to fixing damaged flashing around chimneys and vents, a common source of leaks. We provide emergency roof repair services across Chesapeake, from Great Bridge to Western Branch, because we know that some issues can't wait. Don't let a small leak turn into a major headache. Contact our team for a fast, reliable inspection and repair service that restores the integrity of your roofing system and protects your home's interior from costly damage.

May Anderson - WT Anderson Technical Director
Installation & Permitting Verified

Technical Review by May Anderson

Technical Lead May Anderson (VA CLASS A #2705137326) personally verifies all Chesapeake new roof specifications. Her oversight ensures compliance with VUSBC Chapter 15 and manages the complex Financial Hardship Determination documentation required for modern asphalt shingles in Chesapeake’s historic zones.

See What Our Customers Say
4.9
600+ Reviews
Amazing, FLAWLESS, extensive rebuild of our third-story crow's nest/open porch (three previous attempts by other contractors had failed) and recaulk of entire house by two wonderful guys, Dennis and Danny. The rebuild was complicated and difficult but completed seamlessly, efficiently, and always with their signature kindness, pleasantness, and professionalism.
Fantastic company. Really easy estimate process and quick scheduling. They completed the work (vinyl wrapping all soffits, fascia, windows, porch, and all other exposed wood) 2 days ahead of schedule and to a high standard.
WT Anderson put a new roof on my house and a separate one on a one car garage... My neighbor can see the top of my house and said the roof is beautiful!
WT Anderson is probably the best roofing company in the Hampton Roads area. The work team showed up early worked hard all day, did an outstanding job even stayed late to clean up and ensure that everything was perfect.

Why Homeowners in Chesapeake, VA Trust WT Anderson

  • Local Hampton Roads Expertise: We aren't a storm-chasing company from out of state. We are a family-owned roofing business that lives and works right here in the Chesapeake area. We understand the unique challenges our coastal climate presents, from hurricane-force winds to humid summers. Our team is familiar with all local building codes across Virginia Beach, Norfolk, Portsmouth, Suffolk, and Newport News, ensuring your project is done right and to the highest local standards.
  • Uncompromising Quality & Craftsmanship: We are a certified roofing company committed to excellence. This commitment is reflected in our choice of materials from industry leaders like GAF, Owens Corning, and CertainTeed, and in the skill of our dedicated craftsman team. Our status as a top-rated roofer is backed by a robust workmanship warranty on every roof installation, giving you confidence that your new roof is built to last.
  • A Customer-First Approach: We believe in building lasting relationships based on trust and transparency. From your first call, you'll experience the WT Anderson difference. We provide a comprehensive, free roofing estimate with no hidden fees and no high-pressure sales tactics. Our team takes the time to listen to your needs, explain your options clearly, and keep you informed throughout the entire process, ensuring a smooth and stress-free experience.
  • Complete Exterior Solutions Provider: Your home's exterior is an interconnected system. That's why we provide more than just roofing. Our services include professional gutter installation, siding replacement, skylight installation, and ensuring proper attic ventilation. By offering these integrated services, we provide a single, reliable point of contact for all your exterior remodeling and home improvement needs, guaranteeing that all components work together for maximum protection and performance.

Full Exterior Services in Chesapeake

Gutter & Siding Installation

A high-quality roof is only one part of a complete exterior protection system. Properly installed gutters and siding are essential for safeguarding your home's foundation and structure. We provide expert gutter installation services, ensuring rainwater is channeled safely away from your home to prevent foundation issues, soil erosion, and basement flooding. We also specialize in siding installation, offering a variety of materials that not only protect your home from the harsh Atlantic weather but also dramatically improve its appearance. As a comprehensive exterior remodeling contractor, we ensure your roofing, siding, and gutters work together seamlessly. This integrated approach to home improvement guarantees a cohesive look and superior protection for your entire property, from the top of the roof to the ground.

Roof Inspection & Maintenance

Proactive care is the key to maximizing the lifespan of your roof. Our professional roof inspection service provides a detailed assessment of your roof's condition, identifying potential issues before they escalate into expensive repairs. We recommend annual inspections, especially after major storms common in the Hampton Roads region. During our free roof inspection, our team examines every component, including shingles, roof flashing, ridge vents, soffit and fascia, and attic ventilation. We then provide a clear, honest report and, if needed, a detailed roofing quote for any recommended roof maintenance or repairs. A well-maintained roofing system performs better, lasts longer, and provides consistent peace of mind. Let the trusted local roofing contractors at WT Anderson help you protect your investment with our thorough and reliable maintenance services.

Verified Field Notes

Recent Activity in Chesapeake

Storm Repair: Project Manager Hector Miranda (Navy Vet) resolved a storm-related leak and faulty gutter (Verified July 2025).

Simonton Upgrade: Crew Lead Dennis and PM Jazmine completed a complex window overhaul with a perfect magnetic nail sweep (Verified May 2025).

Speed of Service: Co-Owner Tom Anderson was cited for delivering detailed project estimates within hours of the initial assessment (Verified June 2025).

Protocols including our magnetic nail sweep are verified across 600+ aggregate customer interactions.
Personnel Verification

Field Leadership: Verified Repair Oversight

Expertise: Project Manager Héctor Miranda (Navy Vet) was recently praised for his "professional, honest, and informative" approach while diagnosing complex storm damage for a Chesapeake homeowner (Verified July 2025).

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Our team of friendly experts can assess the needs of your home and provide you with the knowledge you need to make informed decisions.

Never Pushy — No Hidden Costs — Integrity Always
10,000+ Happy Customers
GAF Master Elite® Certified, President's Club
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Factors to Consider Before a New Roof Installation

Local Climate and Weather Patterns

It’s important to consider the climate and weather conditions in your area when choosing a roofing system. Chesapeake experiences a variety of coastal weather, including strong winds, heavy rain, and occasional hurricane threats. Because of this, selecting a durable roofing system that can handle these conditions is essential for protecting your home.

Type of Roofing Material

One of the first factors to consider when installing a new roof is the type of roofing material. Options such as asphalt shingles, metal, and wood each offer different benefits. Asphalt shingles are popular for their affordability and durability, while metal roofing is known for its long lifespan and energy efficiency. Our team can help you compare materials and choose the best option for your home.

The style and appearance of your roof is also important. The right roofing system can improve your home’s curb appeal and overall value. Whether you want a traditional style or a more modern look, we offer options to match your home and preferences.

Warranties Offered by Roofer or Manufacturer

In addition to manufacturer warranties, we also stand behind our work with our own installation warranty. With more than 20 years of experience serving homeowners in Chesapeake and the surrounding Hampton Roads area, our skilled roofing team is committed to delivering reliable workmanship.

While installation issues are rare, our warranty provides added peace of mind. If a problem related to our installation occurs, our team will address and resolve it quickly and professionally.

A Path to Affordability: The Financial Hardship Determination Explained

This is the single most important piece of information for a historic homeowner facing a costly roof replacement in Chesapeake, VA. The city understands that maintaining historical accuracy can be a financial burden. To address this, they created the "Financial Hardship Determination."

A homeowner in a Chesapeake historic district can apply for a 'financial hardship determination' to use modern architectural grade asphalt shingles instead of more expensive historic materials. This isn't an automatic approval; it's a formal process with specific requirements, but for those who qualify, it can reduce the cost of a new roof by tens of thousands of dollars.

How to Qualify and Apply for Financial Hardship

The core of the application process is demonstrating the significant cost difference between the two options. According to the city's guidelines, homeowners must provide two cost estimates from licensed contractors to repair the historic roof and two estimates to replace it with architectural grade asphalt shingles. This documentation is critical. The estimates must be detailed, clear, and from reputable, licensed roofing contractor teams.

This is where choosing the right local roofing experts becomes paramount. You need a team that not only understands how to install a roof but also how to prepare the specific documentation the City of Chesapeake requires. An incomplete or improperly formatted estimate can delay or even derail your application. At WT Anderson, with our 27 years of experience serving homeowners across Hampton Roads, from Chesapeake to Norfolk and Virginia Beach, we are fluent in this process. We provide the detailed, separate estimates you need to build a strong case for your application.

Hiring a Professional Roofer in Chesapeake

Qualifications for Professional Roofers in Chesapeake

In Chesapeake and throughout Hampton Roads, roofing contractors must hold a valid contractor’s license issued by the Virginia Department of Professional and Occupational Regulation (DPOR). This license confirms the contractor has met the required education, experience, and testing standards to perform roofing work in Virginia. WT Anderson is also proud to be a GAF Master Elite® contractor.

Installation Field Logs

Verified Projects: South Hampton Roads Hub

System Precision: Verified by Cline Reasor for a "professionally detailed" new roof installation. Our on-site crew manager, Pedro, was cited for ensuring all technical seams met "tight and sound" code standards before Atlantic storm cycles (Verified Receipt).

Regulatory Success: Our team successfully navigates the BHAR and permitting offices to streamline new installations for neighborhoods from Great Bridge to Hickory.

WT Anderson represents a regional installation portfolio of 1,071+ verified 5-star interactions.

Researching Reputable Companies with Good Reviews

When planning a new roof installation, it’s important to choose a roofing company with a strong reputation and positive customer reviews. With more than 20 years of industry experience and over 600 five-star Google reviews, WT Anderson has built a reputation for delivering dependable roofing services across Chesapeake and the surrounding Hampton Roads communities.

Obtaining Multiple Estimates and Detailed Proposals

We always recommend that homeowners gather multiple estimates before selecting a roofing contractor. Comparing proposals from different companies can help you better understand pricing, materials, and the services offered, allowing you to make a more informed decision for your roofing project.

Choosing the Right Roofing Company in Chesapeake

When you request an estimate from WT Anderson, you’ll receive a detailed proposal outlining the materials we use, the expected project timeline, and clear, transparent pricing. We believe in providing honest information so homeowners can feel confident about their roofing decisions.

Getting multiple estimates can help you compare experience, services, and pricing between companies. When you review our workmanship, expertise, and dedication to quality, we’re confident WT Anderson will stand out.

If you need a new roof installation in Chesapeake, contact our team for a detailed estimate and proposal. With more than 20 years of roofing experience serving Chesapeake and the Hampton Roads area, we’re ready to help with your project.

Why Your Contractor's Local Knowledge Matters More Than You Think

In Chesapeake, especially within historic zones, a roofer's job goes far beyond the physical work of the installation. A truly professional roofing team must be a partner in navigating the complex web of local and state regulations. Simply getting a few roofing quotes isn't enough; you need an insured roofer who understands the system from the inside out.

One client recently shared their experience, noting, "The staff throughout the process was friendly and responsive. The turnaround time from quote to installation exceeded my expectations." This is the standard we strive for. That speed and efficiency aren't just about scheduling; they come from knowing exactly what the Chesapeake permitting office needs, how to document for the BHAR, and how to ensure every component of the job meets Virginia's stringent building codes.

For example, all reroofing work in our state must comply with Chapter 15 of the Virginia Uniform Statewide Building Code (VEBC). Furthermore, specific details like flashing are also highly regulated. The Virginia Residential Code states that metal roof flashing must be corrosion-resistant with a thickness of no less than 0.019 inches. A contractor unfamiliar with these nuances can cause significant delays and inspection failures, turning your straightforward roof replacement into a prolonged headache.

Our experienced roofing team handles everything—from the initial roof inspection service and free roofing estimate to permit acquisition and final sign-off—ensuring a seamless process for you.

Roof Installation FAQs

What is the average cost of a new roof in Virginia?

The average cost for a new roof installation in Virginia, including the Chesapeake and Hampton Roads area, can range widely, typically from $8,000 to $20,000 or more. This price depends heavily on several key factors. The size and pitch (steepness) of your roof are the biggest variables. The type of material you choose also plays a huge role; standard architectural shingles are more affordable than premium options like standing seam metal roofing or slate roofing. Finally, the complexity of the roof, such as the number of valleys, dormers, and skylights, can affect labor costs. The best way to get an accurate figure is to schedule a free roofing estimate, where a professional can assess your specific home and provide a detailed quote.

What is the 25% rule for roofing?

The "25% rule" is a guideline often used in the roofing and insurance industries, particularly concerning roof repair versus replacement. It suggests that if more than 25% of your roof is damaged, it is generally more cost-effective and practical to proceed with a full roof replacement rather than attempting extensive repairs. Patching a large area can lead to an uneven appearance and potential weak points where the new and old materials meet. A full replacement ensures uniform material age, a consistent seal against the elements, and a single, comprehensive material warranty and workmanship warranty for the entire roofing system. Our inspection service can help determine if this rule applies to your situation after assessing the extent of any damage.

How much does it cost to re-roof a 2000 sq ft house?

For a typical 2,000 square foot house in the Chesapeake, VA area, the cost to install a new roof with architectural asphalt shingles generally falls between $9,000 and $16,000. This estimate accounts for the complete process: tearing off the old shingles, inspecting the underlying wood decking and making minor repairs, installing new roof underlayment and flashing, and installing the new shingles and ridge vents. If you opt for higher-end materials like metal roofing, the cost could increase to $20,000-$30,000 or more. We offer various roofing financing options to help make this essential home improvement project more manageable for your budget.

What is the cheapest time of year to get a new roof?

Generally, the "cheapest" time to schedule a roof installation is during the late fall and winter months. This is typically the slow season for local roofing contractors, as demand decreases due to colder weather and holidays. You may find more scheduling flexibility and potentially better pricing from some companies. However, there are trade-offs. Colder temperatures can make shingles more brittle and affect the sealing process. The best time to replace your roof is when it needs it, especially if you have active leaks or storm damage. Delaying a necessary replacement to wait for a "cheaper" season can lead to more expensive water damage repairs inside your home.

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