Finding a trustworthy roofer near you is critical when protecting your home in Southern Maryland. From intense summer storms and high humidity to aging roof systems across Charles, Calvert, and St. Mary’s counties, choosing the right roofing contractor can mean the difference between a long-lasting roof and costly repeat repairs.
This 2026 guide to the top 5 roofing companies in Southern Maryland compares local contractors based on certifications, customer reviews, experience, and service quality. Whether you need roof repair, full replacement, or storm damage restoration, these are the roofers homeowners trust most.
How We Selected the Top 5 Roofers in Southern Maryland
To create this list, we evaluated roofing companies across Charles County, Calvert County, and St. Mary’s County using the following criteria:
Verified Customer Reviews – Google, BBB, and trusted directories
Industry Certifications – Owens Corning, GAF, CertainTeed, Tamko
Service Offerings – Repairs, replacements, storm restoration, inspections
Local Experience – Proven work in Southern Maryland communities
Reputation & Transparency – Licensing, warranties, and professionalism
Each company below includes an overview of services, certifications, and what homeowners should know before choosing them.
1. JDH Remodeling
⭐ 4.9 Rating (400+ Reviews)
🏅 Owens Corning® Platinum Preferred Contractor
📍 Serving Charles, Calvert & St. Mary’s Counties
🌐 jdhremodeling.com
Services Offered
Roof Inspections
Roof Repair
Roof Replacement
Storm Damage Restoration
Attic Ventilation & Insulation
Shingle & Metal Roofing
Gutters, Siding, Windows & Doors
Why Homeowners Choose JDH Remodeling
Family-owned and 3rd-generation since 1986, JDH Remodeling has built one of the strongest reputations in Southern Maryland roofing. As an Owens Corning Platinum Preferred Contractor (MHIC #137491), JDH specializes in high-performance roofing systems designed for Maryland’s storm-prone climate.
Serving communities from Waldorf and La Plata to Prince Frederick, California, Lexington Park, and Mechanicsville, JDH Remodeling is known for detailed inspections, honest recommendations, and workmanship that holds up long-term.
Service Area Coverage:
JDH Remodeling provides professional roofing services throughout Southern Maryland, including Calvert County, Charles County, and St. Mary’s County, with dedicated local teams serving major towns and residential communities across the region.
Best for:
✔ Storm damage restoration
✔ Full roof replacements
✔ VA/FHA-compliant inspections
✔ Homeowners who value longevity over quick fixes
Why JDH Remodeling Ranks #1 in Southern Maryland
| Comparison Factor | JDH Remodeling | Typical Local Roofer |
|---|---|---|
| Years in Business | Since 1986 (3rd Generation) | 5–15 years |
| Manufacturer Certification | Owens Corning® Platinum Preferred Contractor | Standard or mid-tier certifications |
| Licensing & Compliance | MHIC #137491 (Fully Licensed & Insured) | Often not clearly highlighted |
| Roofing Focus | Roof repair, replacement & storm restoration specialists | General exterior services |
| Insurance Claim Support | Documentation & claim assistance included | Limited or homeowner-managed |
| Local Expertise | Deep Southern Maryland housing & weather knowledge | Broad, multi-region coverage |
| Warranties | Manufacturer + workmanship warranties | Limited workmanship coverage |
| Reputation | Consistent 5-star reviews across Google, BBB & Facebook | Mixed or inconsistent reviews |
#2. Southernwood Roofing & Siding
Southernwood Roofing and Siding
⭐ 4.8 Rating | GAF Certified Contractor
Southernwood Roofing & Siding is a well-established contractor known for dependable installations and strong siding expertise throughout Southern Maryland.
Services Offered
Roof Repair & Replacement
Storm Damage Repair
Shingle Roofing
Gutters, Siding, Windows & Doors
Strengths
Solid reputation with consistent reviews
Strong siding and exterior remodeling services
GAF-certified installations
Considerations
Fewer premium roofing system options compared to Owens Corning Platinum contractors
Best For: Homeowners looking for dependable roofing and siding work with manufacturer-backed credentials.
3. Simple Solutions Contracting
Simple Solutions Contracting
⭐ 4.8 Rating | TAMKO Pro Certified
Simple Solutions Contracting delivers practical roofing solutions with a focus on affordability and straightforward project execution.
Services Offered
Roof Repair
Roof Replacement
Storm Damage Repair
Windows, Doors & Siding
Strengths
Competitive pricing
Certified installers for multiple shingle brands
Efficient project timelines
Considerations
Smaller team and regional footprint than top-ranked firms
Best For: Homeowners seeking reliable roofing at a competitive price point.
4. Paramount Property Solutions LLC
Paramount Property Solutions LLC
⭐ 4.9 Rating | Owens Corning Platinum Roofer
Paramount Property Solutions specializes heavily in storm damage restoration, offering hands-on support through insurance claims and emergency repairs.
Services Offered
Roof Inspection
Roof Repair & Replacement
Storm Damage Restoration
Metal & Shingle Roofing
Gutters
Strengths
Strong insurance claims expertise
High customer satisfaction ratings
Platinum-level manufacturer certification
Considerations
Heavily storm-focused; less emphasis on elective upgrades
Best For: Homeowners dealing with insurance claims or severe storm-related roof damage.
5. Capital Renovations LLC
Capital Renovations LLC
⭐ Strong Local Reputation | MHIC Licensed
Capital Renovations LLC is a residential roofing contractor serving Charles County and surrounding Southern Maryland areas, offering practical roofing solutions for homeowners.
Services Offered
Roof Replacement
Roof Repair
Storm & Hail Damage Repair
Asphalt Shingle Roofing
Multi-Family Roofing
Gutters & Exterior Improvements
Strengths
Competitive pricing
Clear communication
Reliable residential roofing services
Considerations
Smaller operational scale
Limited premium roofing system options compared to Platinum contractors
Best For: Homeowners seeking straightforward roofing solutions with transparent pricing.
Why These Roofers Stand Out in Southern Maryland
JDH Remodeling leads with premium systems, longevity, and regional dominance
Southernwood and Paramount offer strong manufacturer-backed reliability
Simple Solutions and Capital Renovations provide cost-effective alternatives
Each company brings value depending on your roofing needs, budget, and location.
Southern Maryland Weather & Roofing Considerations
Southern Maryland experiences:
High humidity
Coastal and inland storms
Seasonal wind events
Tree debris and algae growth
Regular inspections and professionally installed roofing systems are essential for long-term protection.
How to Choose the Right Roofer in Southern Maryland
Verify licensing and certifications
Confirm insurance claim experience if storm damage is involved
Ask about workmanship and manufacturer warranties
Read both positive and negative customer reviews
Request multiple estimates
Get a Free Roof Inspection in Southern Maryland
If you’re planning a roof repair or replacement in Calvert, Charles, or St. Mary’s County, working with a trusted local roofer ensures long-term peace of mind.
Schedule a free roof inspection with a top-rated Southern Maryland roofing contractor today.