The Best Roofing Contractors in Hollywood, MD

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

#1

Southern Maryland Roofing & Exteriors

4.8
(127 reviews)
Verified

A premier full-service roofing contractor specializing in both residential and commercial projects. Known for expert storm damage assessment and working directly with insurance companies to streamline claims. They use high-quality materials and offer robust warranties on both workmanship and materials.

24501 Mervell Dean Road, Hollywood, MD 20636

Specialties & Features

Storm Damage Restoration
Insurance Claim Assistance
Asphalt Shingles
Emergency Tarp-Ups
Roof Inspections

Business Information

Years in Business:15 years
Licensed:Yes
Insured:Yes
#2

Chesapeake Bay Metal Roofing

4.6
(94 reviews)
Verified

Specializes in durable metal roofing systems ideal for Hollywood's coastal climate, offering superior resistance to high winds, heavy rain, and salt air. They also provide expert repair and replacement for asphalt and tile roofs. Highly regarded for their meticulous installation process and focus on energy-efficient solutions.

43950 Commerce Street, Hollywood, MD 20636

Specialties & Features

Metal Roofing Installation
Energy-Efficient Roofing
High-Wind Resistance
Residential Roof Replacement
Tile Roof Repair

Business Information

Years in Business:10 years
Licensed:Yes
Insured:Yes
#3

St. Mary's Roofing & Repair LLC

4.5
(112 reviews)
Verified

A trusted local family-owned business with deep roots in the community. They offer comprehensive roofing services from minor repairs and maintenance to complete replacements. Their team is highly experienced with local building codes and is known for prompt and reliable emergency service, especially after severe storms.

21642 Three Notch Road, Hollywood, MD 20636

Specialties & Features

Emergency Roof Repair
Roof Maintenance Programs
Leak Diagnosis & Repair
Commercial Flat Roofs
Gutter Installation

Business Information

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

Why These Are the Top Roofing Contractors in Hollywood

The roofing market in Hollywood, MD, is heavily influenced by its Chesapeake Bay location, which subjects roofs to high winds, torrential rain from nor'easters and tropical systems, and potential hail. Contractors must be well-versed in wind-rated installations and storm damage restoration. The proximity to Patuxent River NAS also drives demand for both residential and commercial services. Reputable providers distinguish themselves through expertise in navigating insurance claims for weather-related damage.

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 Hollywood regulations and climate

Frequently Asked Questions About Roofing in Hollywood

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

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

For a standard 2,000-2,500 sq. ft. home in Hollywood, a full asphalt shingle roof replacement typically ranges from $12,000 to $25,000. The final cost depends on roof complexity, material quality (e.g., impact-resistant shingles for our coastal storms), and the extent of underlying decking repair needed. Regional material and labor costs in Southern Maryland are generally in line with the national average, but prices can fluctuate with seasonal demand.

2When is the best time of year to schedule a roof replacement in Hollywood, considering the local climate?

The ideal windows are late spring (April-May) and early fall (September-October). These periods typically offer mild, dry weather, which is crucial for proper installation and material adhesion. Summers can be hot and humid, potentially affecting shingle sealing, while our winter months bring unpredictable rain, wind, and occasional freezing temperatures that can delay projects and pose safety risks.

3Are there any specific local building codes or regulations in St. Mary's County that affect roofing projects?

Yes, all roofing work in Hollywood must comply with St. Mary's County building codes, which enforce the 2018 International Residential Code (IRC) with Maryland amendments. A key local requirement is the need for a building permit for any roof replacement. Furthermore, due to our proximity to the Chesapeake Bay and Patuxent River, special wind uplift resistance codes often apply, and your contractor should be familiar with these specific regional provisions.

4How can I verify a roofing contractor is reputable and properly licensed for work in Maryland?

Always choose a contractor licensed as a Home Improvement Contractor (HIC) by the Maryland Home Improvement Commission (MHIC). You can verify their license number online via the MHIC website. Additionally, look for local, established companies with strong references in the Hollywood/Leonardtown area, and confirm they carry both liability insurance and workers' compensation to protect you as the homeowner.

5With the frequent summer thunderstorms and occasional hurricanes, what roof features are most important for durability in Hollywood?

Prioritize impact-resistant shingles (rated Class 3 or 4) to withstand hail and wind-driven debris. Proper attic ventilation is critical to combat our high humidity and prevent moisture damage and ice dams in winter. Ensure your contractor includes high-quality, waterproof underlayment and performs a thorough inspection of flashing—especially around chimneys, vents, and valleys—as these are the most common failure points during our heavy downpours.