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Reliable Roofing Services in Hagerstown, MD Backed by 30+ Years of Experience

A worker installing shingles on the wooden frame of a house roof under a clear sky.

In Hagerstown, MD, homeowners and commercial property owners trust Town and Country Painting & Construction, LLC for dependable roofing solutions that protect their investment from the elements. With more than 30 years of experience serving the Tri-State area, we have built a strong reputation for quality workmanship across all phases of home improvement and construction. From complete roof replacements to detailed repairs and gutter installations, our team delivers results designed to stand the test of time.


A strong roof is one of the most important components of any structure. It shields your property from rain, snow, wind, and seasonal temperature changes. Whether your roof has suffered storm damage, reached the end of its lifespan, or simply needs routine maintenance, we provide professional service tailored to both residential and commercial properties.

Roof Replacement & Repair for Long-Term Protection

Roofing issues should never be ignored. Small leaks or damaged shingles can quickly develop into larger structural problems. Our roofing services focus on durability, safety, and long-term performance.

Professional Gutter Installation & Maintenance

A reliable roofing system includes properly functioning gutters. Without effective water management, even a high-quality roof can experience drainage problems that impact siding, foundations, and landscaping.

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Complete Gutter Installation

We provide full gutter installation services, including 5-inch and 6-inch half round gutters, especially suited for historical homes and buildings. Our contractors are highly skilled in installing both half round and K-type gutters, ensuring proper alignment and secure attachment. These systems are designed to channel water safely away from your structure, helping prevent long-term damage.

A black silhouette icon of a house with a chimney and a sloped roof.

Gutter Cleaning and Repair

Clogged or damaged gutters can lead to water overflow and structural deterioration. Our gutter cleaning and repair services help maintain proper drainage year-round. We remove debris, inspect for damage, and restore functionality to keep your roofing system operating efficiently.

A simple black icon of a house silhouette with a chimney on its sloped roof.

Gutter Covers & Snow Guards

To enhance durability and reduce maintenance, we also install gutter covers that help prevent debris buildup. Snow guards are available to control the movement of snow and ice from your roof during winter months, adding an extra layer of safety and protection.

A worker in white work gloves unrolls a strip of black bitumen roofing material onto a dark, prepared roof surface.
A worker wearing work gloves applies a strip of adhesive roofing membrane to a flat roof surface.
A worker in a high-visibility vest uses a yellow pneumatic nail gun to install grey asphalt shingles on a sloped roof.
Close-up of gray architectural roof shingles covered in a fine layer of morning frost.

Roofing Solutions for Historical & Modern Properties

Our experience includes working on historical homes, churches, farmhouses, subdivision properties, and commercial facilities. Roofing on older structures often requires careful attention to architectural detail and material compatibility. We take pride in preserving the character of historical buildings while upgrading their protective systems.


For newer properties, we focus on modern materials and installation techniques that maximize efficiency and lifespan. Regardless of the property type, our commitment to quality remains consistent.

Our Roofing Inspection & Installation Process

Every roofing project begins with a detailed evaluation. We inspect the condition of shingles, flashing, ventilation, and drainage systems to determine the best course of action. After providing a complimentary estimate, we outline the scope of work and timeline clearly.


During installation or repair, we prioritize safety, cleanliness, and structural integrity. Proper underlayment, flashing placement, and ventilation are critical components of a durable roof. Once the project is complete, we conduct a final inspection to ensure every detail meets our high standards..

A person kneels on a shingled roof, reaching down to inspect a section of shingles in bright sunlight.
A gloved hand marks a spot on a dark asphalt roof shingle with white chalk.
Two workers wearing tool belts remove old, dark asphalt shingles from a residential roof on a sunny day.
A person in an orange high-visibility vest climbs a ladder against the side of a white house to inspect the roof.

Frequently Asked Questions About Our Roofing Services

  • Q: How do I know if my roof needs replacement or just repair?

    A: Visible damage, frequent leaks, missing shingles, and aging materials are common indicators. We perform a thorough inspection to determine the most cost-effective solution.

  • Q: What types of roofing materials do you install?

    A: We primarily install asphalt shingles but also work with flat roofing systems, standing metal seam roofs, and EPDM™ rubber roofing.

  • Q: Are architectural shingles available?

    A: Yes. We offer architectural shingles backed by 35- to 50-year warranties for extended durability and enhanced appearance.

  • Q: Do you install gutters along with roofing projects?

    A: Yes. We provide complete gutter installation, including half round and K-type systems, along with gutter covers and snow guards.

  • Q: Do you serve both residential and commercial clients?

    A: Absolutely. We provide roofing services for homes, churches, commercial buildings, and industrial facilities throughout the Tri-State area.