Roofing & Exterior Contractor in Hollywood, MD
Roof replacements, leak repairs, storm-damage work, gutter guards and siding for Hollywood homes, from Route 235 to the Patuxent shoreline.
Roofing for Hollywood Homes, Inland and on the River
Hollywood stretches from the Route 235 corridor east to the Patuxent River, where waterfront neighborhoods like Drum Cliffs and Hollywood Shores look across the water toward Calvert County. Hollywood Road (Route 245) links it to Leonardtown and runs past Sotterley Plantation, one of the area's best-known historic sites.
Housing here is varied: older homes on large lots, ranchers and colonials in established subdivisions, newer homes along Route 235, and waterfront houses on bluffs and creeks off the Patuxent. Roofs on the water and roofs on wooded inland lots wear out in different ways, and we treat them differently.
HomePro is based in Prince Frederick, on the other side of the Patuxent. We schedule Hollywood work regularly, and every job starts with a free inspection and a photo report.
What We Do for Hollywood Homes & Businesses
The services Hollywood homeowners call us for most. Each has its own detail page.
Roof Repair & Replacement in Hollywood
Repairs or complete replacements for inland and waterfront Hollywood homes.
Learn more →Roof Leak Repair in Hollywood
Wind-driven leaks at flashing, skylights and vents found and fixed at the source.
Learn more →Storm Damage & Insurance Claims in Hollywood
Storm damage on river-facing roofs documented with photos for your claim.
Learn more →Metal Roofing in Hollywood
Standing seam metal for waterfront homes that need a roof built for wind.
Learn more →Seamless Gutters & Gutter Guards in Hollywood
Guards for wooded lots so leaves and needles don't clog gutters every fall.
Learn more →Siding Repair & Replacement in Hollywood
Siding repair and replacement for walls exposed to sun, wind and river moisture.
Learn more →Patuxent Wind and Weather in Hollywood
Waterfront parts of Hollywood face the Patuxent River with a long stretch of open water in front of them, so storms from the east and northeast hit those homes hard. Nor'easters push wind-driven rain under shingle edges and up behind flashing, and tropical storm remnants bring gusts that can lift ridge caps and peel back damaged shingles. Homes on bluffs get the strongest wind.
Moist air off the river wears on exposed fasteners, flashing and wood trim over time. Inland, the bigger risk is trees: wooded lots off Route 235 and Hollywood Road see limb damage in storms and gutters packed with leaves every fall. Summer humidity and winter freeze-thaw cycles round out the list.
Hollywood Homes and the Roofs on Them
Most Hollywood homes have asphalt shingle roofs, from older three-tab roofs on established homes to architectural shingles on newer builds. On waterfront homes, we take extra care with nailing, edge metal and flashing so the roof holds up to wind off the river. Some owners on the water choose standing seam metal for the same reason.
Inland, we see a lot of gutter overflow on wooded lots, rotted fascia, moss on shaded slopes, and roofs that are simply reaching the end of their life. Waterfront properties near the Patuxent may fall within the Critical Area, so we check what St. Mary's County requires for the work before we start.
Free Roof & Exterior Estimate in Hollywood
Tell us about your Hollywood home, inland or on the water, and we'll schedule a free inspection.
- Same-week inspections in Hollywood
- Photos of every problem we find
- Insurance-claim help after storms
- Licensed, insured & warrantied work
Recent Projects Near Hollywood
Roofing, siding and gutter work across St. Mary's County and Southern Maryland.
Where We Work in Hollywood
We serve all of Hollywood, including the Route 235 corridor, Hollywood Road (Route 245), Sotterley Road, and waterfront neighborhoods along the Patuxent like Drum Cliffs and Hollywood Shores. We also cover nearby Leonardtown, California and Mechanicsville.
Hollywood is across the river from our Prince Frederick office, so we plan visits ahead and let you know our timing. Call (443) 771-0755 to set up an inspection.
Hollywood Roofing Questions
What Hollywood homeowners ask us most.
My house faces the Patuxent. Does that change how the roof should be installed?
Yes. Waterfront roofs take more wind and moisture, so we pay close attention to nailing patterns, starter and ridge products, edge metal and flashing. We'll explain what we recommend for your exposure during the inspection.
Is metal roofing worth it on a waterfront home?
For many waterfront homes, standing seam metal is a strong option because it handles wind well and has few exposed seams. We'll walk you through metal and shingle options side by side so you can decide.
My property is near the water. Are there Critical Area rules for roof work?
Waterfront properties may fall within the Chesapeake Bay Critical Area. A roof replacement on an existing home is usually straightforward, but we check what St. Mary's County requires for your property before we start.
My roof only leaks during nor'easters. Why?
That usually means wind is driving rain sideways under shingle edges or behind flashing, often on the side facing the storm. We look for lifted shingles, loose flashing and gaps at walls and chimneys on that side of the roof.
How soon can you inspect my roof in Hollywood?
Most inspections are scheduled within a few days. If you have an active leak after a storm, call (443) 771-0755 and we'll prioritize a temporary fix.
Talk to HomePro Contractors in Hollywood
Free roof inspections in Hollywood and across St. Mary's County. Licensed, insured, and based in Southern Maryland.