Roofing & Exterior Contractor in Leonardtown, MD
Careful roof repairs, replacements, metal roofing, gutters and trim work for Leonardtown's older homes and newer neighborhoods.
Roofing for Leonardtown's Old and New Homes
Leonardtown is the county seat of St. Mary's County and one of the oldest towns in Maryland, founded in 1708 at the head of Breton Bay. Around the town square and along Fenwick Street and Washington Street you'll find older homes and buildings next to newer subdivisions on the edge of town.
Older homes need a different approach than a 2000s colonial. Chimneys, dormers, porch roofs and decades of past repairs all have to be worked around carefully. Newer homes have their own issues, usually builder-grade flashing and ventilation that start to show their limits after 15 to 20 years.
HomePro is based in Prince Frederick and schedules Leonardtown work regularly. Every job starts with a free inspection and a photo report, so you know what you're dealing with before you decide anything.
What We Do for Leonardtown Homes & Businesses
The work Leonardtown homeowners call us for most. Each service has its own detail page.
Roof Repair & Replacement in Leonardtown
Repairs that respect older framing and trim, or a full replacement done right.
Learn more →Roof Leak Repair in Leonardtown
Chimney, dormer and valley leaks traced to the real source, then properly flashed.
Learn more →Roof Inspections in Leonardtown
Photo inspections before you buy an older home or plan a renovation in town.
Learn more →Metal Roofing in Leonardtown
Standing seam metal for main roofs, porches and outbuildings that suit the area's older homes.
Learn more →Gutter Repair & Replacement in Leonardtown
Gutters sized and pitched to handle heavy rain on steep or complicated rooflines.
Learn more →Soffit & Fascia in Leonardtown
Rotted fascia and soffit boards replaced and wrapped so they stay sealed.
Learn more →Breton Bay Weather and Leonardtown Roofs
Leonardtown sits at the head of Breton Bay, a tidal arm of the Potomac River. Storms that come up the Potomac can bring strong gusts, and waterfront and hillside homes catch more of that wind than houses in sheltered spots. Wind-driven rain from summer thunderstorms and nor'easters tests chimney flashing, dormer walls and older valleys first.
Moist air off the water also speeds up wear on wood trim. Fascia boards and soffits that stay damp, especially behind clogged gutters, rot from the back side long before you see it from the ground. In winter, freeze-thaw cycles open small gaps in mortar and flashing, which is why many Leonardtown chimney leaks show up in late winter.
Leonardtown Homes and the Roofs We See
In and around the older part of town, we see steep roofs, brick chimneys, dormers, porch roofs with low-slope sections, and the occasional metal roof. These homes often have several layers of past repairs, so we look closely at decking, flashing and trim before recommending anything. Where a property is in a historic area, we check what the Town of Leonardtown and St. Mary's County require before work starts.
Newer subdivisions around town mostly have asphalt shingle roofs on colonials and ranchers. Common jobs there include replacing worn shingles, adding ridge venting, swapping cracked pipe boots, and fixing fascia behind overflowing gutters.
Free Roof & Exterior Estimate in Leonardtown
Tell us about your Leonardtown home, old or new, and we'll schedule a free inspection with a photo report.
- Same-week inspections in Leonardtown
- Photos of every problem we find
- Insurance-claim help after storms
- Licensed, insured & warrantied work
Recent Projects Near Leonardtown
Roofing, siding and gutter work across St. Mary's County and Southern Maryland.
Where We Work in Leonardtown
We serve all of Leonardtown, including the homes around the town square, Fenwick Street and the wharf on Breton Bay, the neighborhoods along Route 5 and Hollywood Road (Route 245), and homes out toward Breton Bay's shoreline. We also work throughout central St. Mary's County.
Leonardtown is a longer drive from our Prince Frederick office, so we plan visits ahead and keep you posted on timing. Call (443) 771-0755 to set up an inspection.
Leonardtown Roofing Questions
What Leonardtown homeowners ask us most.
My older Leonardtown home has a leak by the chimney. Do I need a new roof?
Not necessarily. Chimney leaks are often caused by failed step or counter flashing, or by worn mortar, not the whole roof. We inspect the chimney and surrounding roof and tell you whether a flashing repair will solve it.
Is a metal roof a good fit for an older home in Leonardtown?
It can be. Standing seam metal suits many older homes, porches and outbuildings, and it handles wind and heavy rain well. We'll show you options and talk through how it would look and perform on your house.
My home is in or near the historic part of town. Are there extra rules?
There can be. We check what the Town of Leonardtown and St. Mary's County require for your property and type of work before scheduling anything.
Why does my fascia keep rotting?
Usually water is getting behind the gutter, either from clogs, missing drip edge or a gutter pitched the wrong way. We replace the damaged wood and fix the cause so it doesn't come back.
How soon can you come out to Leonardtown?
Most inspections are scheduled within a few days. If water is coming in, call (443) 771-0755 and we'll prioritize a temporary fix.
Talk to HomePro Contractors in Leonardtown
Free roof inspections in Leonardtown and across St. Mary's County. Licensed, insured, and based in Southern Maryland.