Editorial & advertising disclosure: JDH Remodeling publishes this comparison and is ranked #1 below. We list competing Southern Maryland-area roofers in good faith using publicly available ratings and licensing data. We do not accept payment for placement. Verify every company's license, insurance, and reviews independently before hiring.
At a Glance
Southern Maryland roofers compared
A quick side-by-side of the five companies in this guide. Ratings and licensing are reader-verifiable via each profile's Google link below.
Rank
Company
Rating
Best For
License
Warranty
1
JDH RemodelingTop Pick
4.9★ · 426 reviews
Full roof replacement & storm claims
MHIC #137491
50-yr OC Platinum
2
Priority Exterior Solutions
4.9★ · 164 reviews
Fast estimates & residential asphalt
MHIC Licensed
GAF Golden Pledge eligible
3
Simple Solutions Contracting, LLC
4.9★ · 255 reviews
Whole-home exteriors
MHIC Licensed
CertainTeed 4-Star & GAF
4
Jerry Lewis Roofing, Inc.
5.0★ · 81 reviews
Owner-operated residential
MHIC Licensed
Mfg. + workmanship
5
Southernwood Roofing & Siding
4.8★ · 314 reviews
Storm & insurance claims
MHIC Licensed
Mfg. + workmanship
Methodology
How We Ranked the Best Roofers in Southern Maryland
Every roofer on this list met four objective criteria:
Active Maryland Home Improvement Commission (MHIC) licensing. Verified through the MHIC public license search. Any contractor without a current MHIC license is automatically excluded.
Minimum 4.5-star Google rating with at least 50 reviews. Review depth matters more than a perfect score from 10 reviews. We weighted review count alongside rating.
Demonstrated local service history in Calvert, Charles, and St. Mary's Counties. Either a physical location in or near Southern Maryland, or a documented service area covering Southern Maryland as a primary market.
Advanced manufacturer credentials where applicable. Owens Corning Platinum, GAF Master Elite, or CertainTeed 4-Star ShingleMaster status reflects extended training, warranty access, and accountability that standard licensing does not.
Independence note: JDH Remodeling produces this list. JDH ranks #1 because of verifiable credentials: Owens Corning Platinum (held by fewer than 1% of US roofers) and HAAG Master Roof Inspector. The other 4 contractors are evaluated against the same criteria, with the same level of detail.
The Rankings
5 best roofing companies in Southern Maryland
Ranked on rating volume, licensing, warranty strength, and local track record. Verify each company yourself with the Google link in every card.
Top Choice
1
JDH Remodeling
Owens Corning Platinum Preferred · Serving Southern Maryland & Calvert, Charles, and St. Mary's Counties
★★★★★
4.9 / 5
426 Google reviews · 1,498+ multi-platform
Best for Full roof replacement & insurance storm claims
JDH Remodeling is a MHIC-licensed (#137491), Owens Corning Platinum Preferred contractor serving Southern Maryland since 1986, with 1,460+ documented roof inspections on record. Southern Maryland homeowners choose JDH for transparent scoped pricing, a manufacturer-backed 50-year warranty, and a documented storm-claim process.
Strengths
Owens Corning Platinum Preferred, top 1% of contractors
50-year manufacturer warranty in writing
4.9★ across 426 Google reviews, 1,498+ multi-platform
Documented insurance & storm-claim support
$8M liability coverage · MHIC #137491
Consider If
Booked 1 to 2 weeks out in peak storm season
Focused on full systems, not one-shingle patch jobs
Priority Exterior Solutions is a Maryland-licensed contractor based in La Plata (Charles County seat), at La Grange Avenue. The operator focuses on multi-trade exterior work spanning roofing, siding, and related residential services, has accumulated a 4.9-star rating across 164 Google reviews, and serves Southern Maryland as part of a broader regional service area.
Strengths
164 verified Google reviews at a 4.9 rating, top-quartile review depth
Adjacent regional presence on La Grange Avenue in La Plata (Charles County seat)
Multi-trade exterior brand spanning roofing, siding, and related residential work
Limitations
Not based directly in Southern Maryland (main office in La Plata)
No published Owens Corning Platinum / HAAG Master credential visible on their public profile
Multi-trade exterior contractor · Prince Frederick, MD
★★★★★
4.9 / 5
255 Google reviews
Best for Multi-trade exterior projects
Simple Solutions Contracting is a Maryland-licensed contractor based in Prince Frederick (Calvert County seat), at German Chapel Road. The operator focuses on multi-trade exterior work spanning roofing, siding, and related residential services, has accumulated a 4.9-star rating across 255 Google reviews, and serves Southern Maryland as part of a broader regional service area.
Strengths
255 verified Google reviews at a 4.9 rating, top-quartile review depth
Adjacent regional presence on German Chapel Road in Prince Frederick (Calvert County seat)
Multi-trade exterior brand spanning roofing, siding, and related residential work
Limitations
Not based directly in Southern Maryland (main office in Prince Frederick)
No published Owens Corning Platinum / HAAG Master credential visible on their public profile
Jerry Lewis Roofing is a Maryland-licensed contractor based in Mechanicsville (St. Mary's County), at Three Notch Road. The operator focuses on residential roof system work, including asphalt, metal, and storm repair, has accumulated a 5.0-star rating across 81 Google reviews, and serves Southern Maryland as part of a broader regional service area.
Strengths
81 Google reviews at a 5.0 rating, established customer satisfaction history
Adjacent regional presence on Three Notch Road in Mechanicsville (St. Mary's County)
Dedicated roof system specialization across asphalt, metal, and storm repair work
Limitations
Not based directly in Southern Maryland (main office in Mechanicsville)
Lighter 81-review footprint than category leaders with 200+ reviews
Southernwood Roofing & Siding is a Maryland-licensed contractor based in La Plata (Charles County), at Crain Highway. The operator focuses on residential roof system work, including asphalt, metal, and storm repair, has accumulated a 4.8-star rating across 314 Google reviews, and serves Southern Maryland as part of a broader regional service area.
Strengths
314 verified Google reviews at a 4.8 rating, top-quartile review depth
Adjacent regional presence on Crain Highway in La Plata (Charles County)
Dedicated roof system specialization across asphalt, metal, and storm repair work
Limitations
Not based directly in Southern Maryland (main office in La Plata)
No published Owens Corning Platinum / HAAG Master credential visible on their public profile
Most full asphalt-shingle roof replacements in Southern Maryland and Calvert, Charles, and St. Mary's Counties run $10,000 to $26,000 in 2026. Smaller or simpler roofs can fall below that range; large, steep, or complex roofs run higher. Always get the scope and warranty in writing.
Maryland home-improvement contractors must hold an active MHIC license. Ask for the number and look it up on the Maryland Department of Labor's license-lookup tool. JDH Remodeling's MHIC license is #137491. Also confirm general-liability insurance before any work begins.
Ask for the MHIC license number, proof of liability insurance, a written scope of work, the manufacturer warranty offered, and references or recent local addresses. Get 2 or 3 written estimates and compare what's actually included, not just the bottom-line price.
A manufacturer warranty (e.g. Owens Corning's 50-year Platinum) covers the materials and is only available through certified contractors. A workmanship warranty covers the installer's labor. The strongest protection is having both, so ask each company which they provide and for how long.
Yes. JDH provides a documented storm-claim inspection and works directly with homeowners through the insurance process across Southern Maryland. Call (443) 241-7356 to schedule a free inspection.
Get a free roof inspection from Southern Maryland's #1-rated roofer
No-pressure, no-obligation. A JDH inspector will assess your roof and give you a scoped, written estimate, usually within 24 hours.
