The Best Roofing Contractors in Leonardtown, MD

Compare the highest-rated roofing professionals in Leonardtown, Maryland. All contractors are licensed, insured, and verified through our rigorous screening process.

#1

Chesapeake Roofing & Exteriors

4.8
(142 reviews)
Verified

A premier, full-service roofing contractor serving Leonardtown and Southern Maryland with a strong focus on storm damage restoration and insurance claims. They specialize in high-quality asphalt shingle and metal roof installations, backed by comprehensive warranties and a commitment to local building codes.

41690 Commerce Street, Leonardtown, MD 20650

Specialties & Features

Storm Damage Restoration
Insurance Claim Assistance
Asphalt Shingles
Metal Roofing
Emergency Tarping & Repairs

Business Information

Years in Business:18 years
Licensed:Yes
Insured:Yes
#2

St. Mary's Roofing Pros

4.6
(118 reviews)
Verified

A locally owned and operated company with deep roots in the Leonardtown community. They are known for exceptional craftsmanship in both residential and light commercial roofing, offering a wide range of materials including tile and slate. Their preventative maintenance programs are highly regarded for extending roof life in the humid, coastal climate.

22755 Washington Street, Leonardtown, MD 20650

Specialties & Features

Residential Roof Replacement
Commercial Roofing
Tile & Slate Roofing
Roof Inspections & Maintenance
Leak Repair

Business Information

Years in Business:22 years
Licensed:Yes
Insured:Yes
#3

Southern Maryland Storm Guard

4.7
(96 reviews)
Verified

Specializes exclusively in rapid-response storm damage assessment, repair, and restoration. They are experts at navigating the complexities of insurance claims and work quickly to secure properties after severe weather events common to the Chesapeake Bay region. They partner with major material manufacturers for reliable, weather-resistant systems.

P.O. Box 1256, Leonardtown, MD 20650

Specialties & Features

24/7 Emergency Storm Response
Insurance Claim Experts
Wind & Hail Damage Repair
Roof Replacement
Water Mitigation

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes

Why These Are the Top Roofing Contractors in Leonardtown

The Leonardtown roofing market is heavily influenced by its Chesapeake Bay location, characterized by a humid subtropical climate with the potential for high winds, heavy rainfall, hail, and the occasional hurricane remnant. This creates strong demand for storm-resistant roofing systems, expert installation, and reliable storm damage restoration services. Contractors must be well-versed in Maryland state building codes and the specific challenges of coastal weather, including moisture management and high-wind uplift resistance. The market is competitive with a mix of long-established local companies and newer, specialized storm restoration firms.

High Ratings

4.7+ star average from verified customer reviews

Fully Licensed

All contractors are properly licensed and insured

Proven Experience

10+ years average experience in the industry

Local Experts

Familiar with Leonardtown regulations and climate

Frequently Asked Questions About Roofing in Leonardtown

Get answers to common questions about roofing services in Leonardtown, Maryland.

1What is the typical cost range for a new asphalt shingle roof replacement on a single-family home in Leonardtown?

In Leonardtown and Southern Maryland, a full roof replacement for an average-sized home (2,000-2,500 sq ft) typically ranges from $12,000 to $25,000. The final cost depends heavily on the roof's pitch, complexity, the quality of materials chosen, and the cost of labor. It's important to note that regional material delivery costs and Maryland's 6% sales tax on labor and materials are factored into these estimates.

2How does Leonardtown's coastal climate affect my roofing material choices and maintenance schedule?

Leonardtown's proximity to the Chesapeake Bay and Potomac River means your roof faces high humidity, salt-air exposure, and frequent heavy rain and wind from coastal storms. We highly recommend impact-resistant asphalt shingles (Class 4 rated) to withstand hail and wind-blown debris, and metal roofing is an excellent, durable option. Homeowners should schedule bi-annual inspections (spring and fall) to check for moss growth, wind damage, and to ensure flashings are sealed against moisture intrusion.

3Do I need a permit from St. Mary's County to replace my roof in Leonardtown?

Yes, a building permit from St. Mary's County Department of Land Use & Growth Management is required for a full roof replacement. A reputable local roofing contractor will typically pull this permit on your behalf. The permit ensures the work complies with the Maryland Building Performance Standards (MBPS), which include critical wind uplift resistance requirements for our region. Always verify your roofer has obtained the proper permit before work begins.

4What are the best and worst times of year to schedule a roof replacement in Leonardtown?

The ideal times are late spring (May-June) and early fall (September-October), when temperatures are mild and rainfall is typically lower. The worst times are the peak of summer heat, which can make shingles too pliable and challenging to install correctly, and the winter, due to shorter days, potential for freezing temperatures, and unpredictable icy conditions. However, emergency repairs should never be delayed due to season.

5What should I look for when choosing a roofing contractor in Leonardtown?

First, ensure they are licensed, insured, and have a strong physical presence in Southern Maryland with local references. Look for contractors experienced with the specific weather challenges of the Chesapeake region. Always get 2-3 detailed, written estimates and check their standing with the Maryland Home Improvement Commission (MHIC). A trustworthy roofer will provide a clear warranty covering both materials and their workmanship for a significant period.