Hollywood sits along the Patuxent River in central St. Mary's County, just north of Leonardtown and a short drive from Patuxent River Naval Air Station.
Homes here face the same hazard profile that drove the May 22, 2025 Lexington Park hail line and the 2020 Isaias tornado near Leonardtown: tropical-system wind, spring hail, and high coastal humidity.
Choosing a roofer in 20636 is not a search-ranking decision. It is a risk decision for the next two decades of Chesapeake-adjacent weather.
This list was built the hard way. Each of the 5 companies below was cross-checked in the Maryland Home Improvement Commission (MHIC) license database, reviewed across Google, BBB, Angi, and Yelp, verified against manufacturer certifications (GAF, Owens Corning, CertainTeed, HAAG), and confirmed as actively servicing St. Mary's County. After comparing dozens of central St. Mary's roofers near Pax River, companies like JDH Remodeling, Hyper Roofing, Sharp's Contracting, LLC, Southernwood Roofing & Siding, and Priority Exterior Solutions rose to the top of the 2026 Hollywood list.
If you live in Hollywood, Leonardtown, California, Mechanicsville, Great Mills, or Lexington Park, these are the five roofers worth a phone call in 2026. Every pick is licensed in Maryland. Every review quote is real and sourced.
Top Rated Contractor
1. JDH Remodeling (Best Overall for Hollywood Homes)
Company Overview
JDH Remodeling is the most-reviewed and most-credentialed roofer serving Hollywood in 2026. Founded in 1986, this third-generation, family-owned company is committed to using only top quality materials and delivering efficient project completion for both residential and commercial clients.
Website:
jdhremodeling.com
MHIC License:
137491
Virginia License:
Class A #2705192986
Founded:
1986 (40 years)
Credentials That Matter
- GAF Master Elite® Certified Contractor (Top 2% nationally).
- HAAG Master Level certified roof inspectors.
- Owens Corning Platinum Preferred Contractor.
- Carries $8 million in liability coverage.
Best For
Hollywood homeowners who want a credentialed generalist for full roof replacement, storm claims, or multi-trade exterior work. JDH handles both residential and commercial projects with a focus on paperwork accuracy and warranty depth.
What Customers Say
"JDH Remodeling recently replaced my roof after hail damage. They clearly explained the processes and installation. Meticulous cleanup."
"MVP performance. He drove 90 minutes after hours for an emergency tarping. Grateful for the clear communication and confidence."
"The work was done on time and the communication was exceptional. I would not hesitate to use this company again."
Top Rated Contractor
2. Hyper Roofing (Best for Honest Repair-First Diagnosis)
Company Overview
Hyper Roofing is the only roofer on this list with a perfect 5.0 star rating across its entire Google history. Based in Waldorf, the company is led by Rob O’Neal and Emerson, and it has built a reputation for integrity, honest inspections, transparent pricing, and a refusal to upsell replacement when repair will do. Hyper Roofing is experienced in dealing with insurance claims and storm damage, ensuring clients receive efficient solutions and support throughout the process. Their commitment to quality work and efficient service sets them apart as a trusted choice for roofing needs.
Credentials That Matter
- GAF Certified Roofing Contractor.
- Our team undergoes ongoing training and holds industry certifications to ensure the highest standards in roofing and gutter services.
- 5.0 out of 5 star rating across 100+ Google reviews, plus 5/5 on GAF’s own contractor review system.
- Public adjuster experience on the team, which is useful when insurance carriers approve only partial claims.
- Serves Maryland, Virginia, and Kentucky (multi-state reach signals bonding depth).
Best For
Hollywood homeowners with an ambiguous leak, an insurance claim that was partially denied, or a flat roof (commercial or residential addition) can rely on Hyper Roofing’s expertise. Hyper’s willingness to recommend repair instead of replacement saves 5-figure quotes for homeowners who do not actually need a new roof yet. In addition, Hyper Roofing can restore roofs after storm damage and has extensive experience with commercial roofing projects, ensuring durability and operational continuity for businesses.
What Customers Say
"I asked Hyper Roofing for a replacement quote, but instead of pushing a sale, Rob and Emerson did a full inspection and told me my roof was still in good shape. I really appreciate their honesty and thoroughness. Highly recommend. Verified Google review (5 stars) | View review"
"We hired Rob to work on our flat roof, and he proved to be incredibly reliable, communicative, and fairly priced. When our insurance company initially approved only half of the roof for replacement after a major storm, Rob, as a public adjuster, challenged their decision and successfully secured full coverage. Verified Google review (5 stars) | View review"
"Hyper Roofing replaced our skylights and repaired part of the roof. Emerson was professional, courteous, and kept us updated every step of the way with clear communication. They did exactly what they promised, on time, and the finished work looks great. Verified Google review (5 stars) | View review"
Top Rated Contractor - 03
3. Sharp's Contracting, LLC (Best Multi-Trade Southern MD Family-Owned)
Company Overview
Sharp’s Contracting, LLC is a family-owned Southern Maryland roofer with 21 years of continuous operation, taking pride in serving clients with exceptional attention to detail. Based in Brandywine and owned by Chris Stokes, the company services southern Anne Arundel, Charles, Prince George’s, Calvert, and St. Mary’s counties.
Their trade menu is unusually broad: roofing, siding, decks, porches, gutters, exteriors, and window installations—along with interior renovations—all under one contract.
Location:
Brandywine, MD
Website:
sharpsroofingandsiding.com
Founded:
2004
MHIC License:
Active, verify before hiring
Credentials That Matter
- Bonded, insured, and fully MHIC licensed with 20+ years of tenure.
- Ongoing professional training ensures our team delivers quality work that meets the highest industry standards.
- 142 Google reviews with 135 at five stars (95% five-star rate).
- One of the few multi-trade Southern Maryland contractors that will also handle decks, porches, and interior renovations under the same contract.
- Works in Southern Anne Arundel and Prince George’s counties in addition to Charles and Calvert, giving it the widest overlap with Dunkirk for commute logistics.
Best For
Hollywood homeowners and commercial clients seeking a long-tenured local contractor for multi-trade exterior work including roofing, siding, and gutters or those needing a contractor who can also finish interior repairs caused by a roof leak will find Sharp’s Contracting an ideal choice. Sharp’s is the strongest “one call, multiple trades” option on this list for older Hollywood homes, and they can restore exteriors after damage to ensure your property is returned to optimal condition.
What Customers Say
"Great experience. Crew was professional, on time, and the end product was high-quality. The roof and gutters look excellent, communication was clear, and everything was done exactly as promised. Highly recommend Sharp's Contracting, LLC. Verified Google review (5 stars) | View review"
"Sharp's really helped me out. I was faced with terrible weather coming and nowhere to turn. Sharp's came to my aid and made repairs to my home before the storm hit, saving me very costly repairs if they hadn't been there. This is what I call service up and beyond. Verified Google review (5 stars) | View review"
"Had windows and doors installed by their fabulous crew. Had them come back and install a storm door. Again service was great. They did an awesome job. Verified Google review (5 stars) | View review"
Top Rated Contractor - 04
4. Southernwood Roofing & Siding (Best GAF-Level Contractor)
Company Overview
Southernwood Roofing & Siding is the most-established Southern Maryland roofing contractor on this list. With more than 20 years in the trade and a BBB A+ accreditation dating to 2014, the company is known for its expertise in storm damage restoration, use of top quality materials, and ability to handle both residential and commercial roofing projects including flat and sloped roofs. Southernwood has quietly built a deep book of storm and hail work across Calvert, Charles, and St. Mary’s counties.
Location:
5895 Crain Highway, La Plata, MD 20646
Website:
southernwoodllc.com
MHIC License:
130434
Virginia License:
2705172343
BBB Status:
A+ Accredited since 2014
Credentials That Matter
- 300+ verified customer reviews averaging 4.9 stars.
- Dual-state licensed (Maryland and Virginia), useful for homeowners who own property on both sides of the Potomac.
- Holds GAF Master Elite® certification—a prestigious status earned by only 2% of roofers nationwide—enabling access to exclusive warranties such as the Golden Pledge® Limited Warranty on qualifying roof systems.
- Ongoing professional training ensures our team meets the highest standards of quality, safety, and industry best practices.
- Offers roofing, siding, windows, doors, and gutters as a single-contract exterior solution.
- Transferable workmanship warranty backed by a manufacturer-certified install.
Best For
Hollywood homes that took a hail or wind hit and want one contractor to handle roof, siding, and gutters under one project manager will benefit from Southernwood’s complete roofing solutions for both residential and commercial clients. Southernwood’s dual-trade staffing is a strong fit for 1990s-and-older housing stock with matching-exterior decisions.
What Customers Say
"I'm so glad we called Southernwood Roofing & Siding right away to replace our roof and siding damaged by a hail storm. Geddy, Tony, and the entire crew did a great job. Verified Google review (5 stars) | View review"
"Southernwood Roofing & Siding did an outstanding job in repairing my roof and siding after the recent wind storm in my area. I will use their services again. Prices are reasonable. Verified Google review (5 stars) | View review"
"Had storm damage. Technician came out within hours. Had an estimate same day and repair made next morning. Very responsive and I am very satisfied with the results. Verified Google review (5 stars) | View review"
Top Rated Contractor - 05
5. Priority Exterior Solutions (Best for Insurance Storm Claims)
Company Overview
Priority Exterior Solutions is a Southern Maryland restoration contractor built specifically around the insurance-claim workflow, with expertise in storm damage restoration and extensive experience dealing with insurance to help clients recover quickly and efficiently. Based in La Plata and licensed under MHIC 148549, the company has quietly accumulated 265+ Birdeye reviews.
Priority is committed to integrity in every project, restoring roofs, siding, and exteriors to optimal condition while providing efficient service and solutions tailored to client needs. They position themselves as an end-to-end storm restoration partner (roof, siding, interior water damage) rather than a pure new-construction roofer.
Location:
105 La Grange Ave, La Plata, MD 20646
Phone:(301) 327-5440
Website:
priorityrr.com
MHIC License:
148549
Credentials That Matter
- Licensed Maryland restoration contractor (MHIC 148549).
- Ongoing professional training and certifications ensure our team delivers quality work that meets the highest industry standards.
- 265+ Birdeye reviews at strong aggregate ratings.
- Angi-listed with active accreditation (as “Priority Restoration”).
- Full exterior and interior restoration capability (useful when a storm damages the roof AND causes interior water damage).
- Insurance-claim-first workflow with documented communication protocol.
Best For
Hollywood homeowners and commercial clients navigating an active insurance claim after a tropical system or hail event, especially when interior water damage is also involved, can rely on Priority for complete roofing solutions. Priority’s restoration-first structure shortens the back-and-forth between adjuster, carrier, and contractor, ensuring a seamless experience for all clients.
What Customers Say
"I had storm damage to my roof and Priority Roofing came in and took care of everything. They work with you, great communication and quality service. My new roof looks amazing. Thank you. Verified Google review (5 stars) | View review"
"Priority was amazing to work with. He was super responsive, advocated for me with the insurance company when they didn’t think the damage should be a covered repair, and were very affordable and able to schedule my roof repair within a couple of days. It was an all around great experience. Verified Google review (5 stars) | View review"
"The roof looks beautiful, and the workmen were quick and capable. The clean-up was excellent. This company went above and beyond the necessary to be sure we were more than satisfied with their work. Verified Google review (5 stars) | View review"