Leonardtown MD Roofing Contractor Historic District, Breton Bay & the St. Mary's County Seat.
JDH Remodeling is Leonardtown, MD's family-owned roofing and exterior contractor for the only incorporated town in St. Mary's County and the 4th-oldest town in Maryland (founded 1660 as Seymour Town, predating Annapolis by 36 years). We have completed 18 jobs inside the Leonardtown 20650 footprint plus the USPS-shared Compton 20627, Clements 20624, Bushwood 20618, and Park Hall 20653 ring, with documented work across the Leonardtown Historic District, Clarks Rest, Society Hill, the Tudor Hall estate area, the Breton Bay shoreline, and the Leonardtown Wharf revitalization corridor. Leonardtown sits at the convergence of three contexts no other JDH service area touches: the National Register downtown historic district anchored by Tudor Hall (Georgian brick 1798, listed 1973), St. Andrew's Church (listed 1973), the Old Jail Museum (1858), and the Leonardtown Courthouse where preservation-aware spec governs visible exterior work on heritage buildings; the St. Mary's County seat institutional workforce orbit of the county courthouse and the Department of Land Use and Growth Management permit office (physically inside Leonardtown at 23150 Leonard Hall Drive) plus MedStar St. Mary's Hospital, St. Mary's Ryken HS, top-rated Leonardtown HS, and the College of Southern Maryland satellite; and the Breton Bay tidal Potomac tributary waterfront pocket with the Breton Bay country club community plus the Leonardtown Wharf waterfront park, Port of Leonardtown Winery, and the post-2008 downtown revitalization wave (First Friday arts, Wednesday farmers market, restaurant cluster). HAAG Master Certified, Owens Corning Platinum Preferred, James Hardie Elite, ProVia Platinum, 50-year non-prorated warranty. MHIC #137491, BBB A+, 1,400+ reviews at 4.9 stars.
How Much Does a Roof Cost in Leonardtown, MD?
Most Leonardtown, MD homes across the 20650 footprint (1,800 to 2,400 sq ft surface) run $9,500 to $16,500 for a full Owens Corning Platinum roof system in 2026; smaller older downtown-adjacent cottages and Compton or Clements rural-residential homes (1,400 to 1,800 sq ft) sit at $7,500 to $11,500, while newer Clarks Rest and Breton Bay country club community 2,400-to-3,000 sq ft colonials reach $12,000 to $18,500, and Breton Bay waterfront homes with coastal-rated spec or Leonardtown Historic District homes with preservation-aware spec (approved dimensional asphalt in historically-appropriate colors, occasional standing-seam metal or cedar shake) can run $14,000 to $32,000. JDH Remodeling has completed 18 Leonardtown roofs across the historic district, Clarks Rest, Society Hill, the Tudor Hall area, and the Breton Bay shoreline since 1986 from headquarters 32 minutes north in St Leonard, and stands behind every install with HAAG Master plus OC Platinum credentials and a transferable warranty. MHIC #137491.
Services We Offer Across Leonardtown, MD
Leonardtown, MD is the only incorporated municipality in St. Mary's County and the county seat, organized across four distinct housing-stock pockets sitting on the MD-5 / Point Lookout Road spine, and a contractor that quotes them all the same way is not actually local. Pocket one: the National Register Leonardtown Historic District in the downtown 20650 core where preservation-aware spec governs visible exterior work on heritage buildings anchored by Tudor Hall (Georgian brick 1798), St. Andrew's Church (listed 1973), the Old Jail Museum (1858), and the Leonardtown Courthouse (around 1930). Pocket two: the older downtown-adjacent cottages plus the rural-residential housing pool around Compton 20627, Clements 20624, and Bushwood 20618 sitting on smaller 1,400-to-1,800 sq ft footprints, typically on the second or third asphalt shingle replacement cycle. Pocket three: the 1990s through 2010s suburban-residential stock across Clarks Rest (the large post-2010 planned subdivision on the eastern edge along MD-5), Society Hill, and the Tudor Hall area, plus the school-zone family premium around Leonardtown HS and St. Mary's Ryken HS, now on the first or second replacement cycle and representing the bulk of our Leonardtown portfolio. Pocket four: the Breton Bay country club community waterfront pocket plus the Leonardtown Wharf revitalization corridor where premium-spec coastal-rated installs (stainless fasteners, Class 4 impact, coastal underlayment) drive the upper band. We install all six exterior trades with the same crew standard regardless of pocket: HAAG Master Certified inspections, fixed pricing locked before tear-off, a 5-year workmanship warranty on top of manufacturer coverage, and Maryland MHIC #137491 on every job.
Roofing
Full Owens Corning Platinum architectural shingle systems with the Duration named-color portfolio matched to the photo evidence we already have from neighboring streets across Clarks Rest, Society Hill, the Tudor Hall area, and the Breton Bay shoreline (our Leonardtown WP cache includes documented Driftwood and Aged Copper installs in 20650). Preservation-aware specification path for the Leonardtown Historic District downtown core: dimensional asphalt in historically-appropriate muted palettes (matching the 18th and 19th century character anchored by Tudor Hall, St. Andrew's Church, the Old Jail Museum, and the Leonardtown Courthouse), occasional standing-seam metal or Western Red Cedar shake for the highest-tier downtown heritage buildings. 50-year non-prorated warranty, transferable for the next sale. HAAG Master Certified diagnostic standard #992109047 on every quote, MHIC #137491 on every install.
Roofing services →
Siding
James Hardie ColorPlus fiber cement and ProVia CedarMAX insulated vinyl. Faithful re-skin profiles for the 1990s through 2010s Clarks Rest, Society Hill, and Tudor Hall area colonial and split-level stock where the original first-generation vinyl has reached the end of its cycle, plus modern-farmhouse and board-and-batten profiles for the newer eastern-edge Clarks Rest subdivisions where homeowners are upgrading curb appeal ahead of resale. Historic-appropriate clapboard and beaded-edge profiles for the Leonardtown Historic District downtown core. Breton Bay country club waterfront homes get the salt-spray-rated ColorPlus fiber cement spec (vs vinyl) on the bay-facing exposures, the same spec JDH installs on Potomac and Patuxent-side homes elsewhere in St. Mary's County.
Siding services →Windows
ProVia Endure double-hung, casement, bay, and bow windows. Energy Star-rated glass packages built for the St. Mary's County humid Köppen Cfa subtropical summers and the institutional-workforce thermostat budget anchored by the county courthouse, MedStar St. Mary's Hospital staff, Leonardtown HS and Ryken HS faculty, and CSM-satellite households. Common upgrade for the original builder-grade sash on 1990s through 2000s Clarks Rest and Society Hill homes plus the older Compton, Clements, and Bushwood rural-residential pool. Historic-appropriate true divided light or simulated divided light options for the downtown Leonardtown Historic District heritage buildings around Tudor Hall and St. Andrew's Church.
Window services →Doors
ProVia Platinum fiberglass entry doors, steel storm doors, and patio sliders. Original 1990s through 2000s entry doors on Clarks Rest, Society Hill, and Tudor Hall area homes are typically on their first or second replacement; we bundle door swaps with roof and gutter work on a single visit when it makes sense for the county-seat institutional-workforce scheduling window. Historic-appropriate wood and wood-grain fiberglass options for the downtown Leonardtown Historic District heritage buildings, with hardware finishes that match the 18th and 19th century character anchored by Tudor Hall and St. Andrew's Church.
Door services →Gutters
Custom seamless K-style gutters with foundation-drainage routing. Critical for the Clarks Rest and Society Hill 2-story colonials where roof runoff has nowhere to go but the slab during the kind of 3-plus-inch summer thunderstorm the mid-Atlantic squall belt can drop in a single afternoon (Tropical Storm Isaias on August 4, 2020 spawned a documented EF-1 tornado near Leonardtown plus benchmark Breton Bay tributary flooding). Bay-facing Breton Bay country club waterfront installs get stainless hangers and oversized downspouts for the wind-driven Potomac-tributary squall events. Maintenance-friendly access for the rural-residential Compton, Clements, and Bushwood housing pool.
Gutter services →
Insulation & Cert
Owens Corning attic insulation, air sealing to Maryland code (R-49 minimum), plus VA, FHA, HUD, and conventional pre-sale roof certifications. Critical for the Leonardtown pre-listing seller running the resale window inside a Clarks Rest, Society Hill, or downtown listing cycle, and for the institutional-workforce relocation cycle around the St. Mary's County government, MedStar St. Mary's Hospital, and the Pax River civilian-contractor commute pool (~25 min south via MD-5). Most older Compton, Clements, and Bushwood pre-1990 rural-residential homes were built to R-19 or less and pay the upgrade back in 4 to 6 years on the Southern MD cooling and heating load.
Insulation services →What's Different About Leonardtown MD Homes
Leonardtown, MD is the only incorporated municipality in St. Mary's County and the 4th-oldest town in Maryland, founded 1660 as Seymour Town and renamed for Benedict Leonard Calvert circa 1728 (Leonardtown predates Annapolis by 36 years), incorporated 1858 with an elected mayor and council. The 2020 census recorded 4,563 residents (up 55.7 percent from 2,930 in 2010, one of the fastest-growing towns in Southern MD) across 3.25 square miles at 85 feet elevation in a humid subtropical Köppen Cfa climate. Three things define how we work this town:
Leonardtown Historic District + Tudor Hall, St. Andrew's Church & Preservation-Aware Roofing on a 1660-Founded Town
Leonardtown holds an architectural-heritage stack no other JDH service area touches. The Leonardtown Historic District (downtown core) is on the National Register of Historic Places and anchors a 1660-founded town that predates Annapolis (1696). Inside the district: Tudor Hall (Georgian brick 1798, listed on the National Register April 26 1973, now St. Mary's County Historical Society headquarters), St. Andrew's Church (listed 1973), the Old Jail Museum (1858), and the Leonardtown Courthouse (circa 1930) anchor a downtown that still hosts restored 18th and 19th century buildings around Leonardtown Square. The St. Mary's County Historic Preservation Commission reviews exterior work within designated historic districts in the county, including Leonardtown. Visible exterior roofing changes on heritage buildings may trigger HPC review for material and color, and acceptable spec runs to dimensional architectural shingles in historically-appropriate muted palettes, occasional standing-seam metal, or Western Red Cedar shake for the highest-tier downtown buildings rather than the brighter named-color portfolio JDH installs elsewhere. The post-2008 downtown revitalization wave (Leonardtown Square First Friday arts events, Wednesday farmers market, Port of Leonardtown Winery, McIntosh Run paddle trail, restored historic buildings hosting the restaurant and gallery cluster) sustains the heritage-tourism economy that anchors homeowner expectations of preservation-aware exterior work.
HAAG Master Certified inspection #992109047 documenting the preservation-aware spec (dimensional asphalt in historically-appropriate palettes, occasional standing-seam metal or cedar shake on highest-tier downtown heritage buildings). St. Mary's County HPC application timing built into the project schedule at no extra charge when triggered. MHIC #137491 on every install. Color and profile portfolio matched to neighboring historic-district comps so the curb appeal reads correctly to the HPC and the next buyer. This is the only credential stack in the Leonardtown market (HAAG Master + OC Platinum + James Hardie Elite + ProVia Platinum + MHIC + third-generation 1986 tenure) for historic-district preservation-aware roofing on a 1660-founded town.
St. Mary's County Seat + County Courthouse, MedStar St. Mary's Hospital, Leonardtown HS and Ryken HS Institutional Workforce
Leonardtown is the only incorporated municipality in St. Mary's County and the county seat, anchoring an institutional workforce profile no other JDH service area touches. The county courthouse, the Department of Public Works, the Department of Land Use and Growth Management (DLU and GM) permit office at 23150 Leonard Hall Drive, the sheriff's office, and multiple county agencies all sit inside Leonardtown 20650, producing a stable upper-middle-band public-sector workforce. Layer the largest civilian employer in St. Mary's County on top: MedStar St. Mary's Hospital, which drives a nurse, physician, and healthcare admin density. Add the education anchors: St. Mary's Ryken HS (private Catholic college-prep drawing families across Southern MD), Leonardtown HS (top-rated public HS in the county with a deep school-zone family premium distinct from the Huntingtown HS catchment further north), Leonardtown Middle, Leonardtown Elementary, the Father Andrew White private school, and the College of Southern Maryland satellite campus with its aquatic center. Add the secondary commuter pool to NAS Patuxent River 25 minutes south via MD-5 (civilian contractor and tenant-command workforce). This combined institutional-workforce anchor produces a multi-decade-tenure homeowner profile (county-seat anchors generations who do not relocate, structurally distinct from the Lexington Park PCS rotation churn and the California MD Wildewood transient-tech mix). Multi-decade tenure drives roof + siding + window combo replacement cycles over 30 to 40 years, the highest lifetime-customer-value profile JDH sees anywhere in St. Mary's County.
Convenient permit-pull: the St. Mary's County DLU and GM permit office is physically IN Leonardtown at 23150 Leonard Hall Drive, so permits get filed and picked up in the same trip as the inspection (a differentiator no sibling-city in St. Mary's County can match because Leonardtown is where the county permit office lives). Pre-listing inspections turned around inside a week with written 5-year-of-life-remaining attestations for the institutional-workforce relocation cycle (county-government, hospital, school, or Pax River civilian-contractor moves). State Farm, USAA, Allstate, Liberty Mutual, and Travelers claim documentation written in the format each carrier's adjuster expects. Single-visit combo projects (roof plus gutters plus door swap) so the multi-decade-tenure homeowner isn't burning multiple weekends on the project. Crews packed alongside our daily California, Hollywood, and Lexington Park work out of St Leonard HQ (32 minutes north via MD-235 and MD-4).
1990s-2010s Clarks Rest, Society Hill, Tudor Hall Area + Breton Bay Waterfront + Rural Compton, Clements and Bushwood Replacement Cycle
The bulk of Leonardtown housing sits in three distinct replacement-cycle waves the in-market competitors don't write to. Wave one: the 1990s through 2010s Clarks Rest (the large post-2010 planned subdivision on the eastern edge along MD-5), Society Hill, and Tudor Hall area 2-story colonials that are now 15 to 35 years past original build and on the FIRST or SECOND asphalt shingle replacement cycle (typical service life of 22 to 28 years on the original builder-grade roofs). Wave two: the Breton Bay country club community waterfront pocket plus the Leonardtown Wharf adjacent residential where premium-spec coastal-rated installs (stainless fasteners, Class 4 impact-rated shingles, coastal underlayment) drive the upper price band, distinct from the inland-only sibling cities. Wave three: the rural-residential housing pool around Compton 20627, Clements 20624, and Bushwood 20618 (USPS-shared with Leonardtown) plus the downtown-adjacent cottage stock, sitting on smaller 1,400 to 1,800 sq ft footprints and well into the SECOND or THIRD asphalt shingle replacement cycle, supporting a deep first-time-homebuyer and rural-tenure market that the in-market competitors all miss because they price the whole town as if it were one suburban subdivision.
Written first or second-replacement-cycle scope documenting the prior-cycle builder-grade material spec vs the OC Platinum upgrade. Color-match portfolio with photo proof from neighboring Clarks Rest, Society Hill, Tudor Hall area, Compton, or Clements homes so the curb appeal sells the comp (our Leonardtown WP cache includes documented Owens Corning Duration Driftwood and Aged Copper installs in 20650). Breton Bay waterfront homes get the upgraded coastal-rated spec (stainless fasteners, Class 4 impact, coastal underlayment) priced into the written quote upfront. Multi-carrier insurance familiarity (State Farm, USAA, Allstate, Liberty Mutual, Travelers) for the storm-claim subset including the May 22, 2025 hail event that hit Leonardtown plus the August 4, 2020 Tropical Storm Isaias EF-1 tornado near Leonardtown. The 18 Leonardtown-direct jobs in 20650 are the proof point, packed alongside JDH's broader 1,400+ review base across the St. Mary's County footprint.
Why Leonardtown MD Homeowners Choose JDH
JDH Remodeling has completed 18 jobs inside the Leonardtown 20650 footprint plus the USPS-shared Compton 20627, Clements 20624, Bushwood 20618, and Park Hall 20653 ring, with documented Owens Corning Duration Driftwood and Aged Copper installs across Clarks Rest, Society Hill, the Tudor Hall area, and the Breton Bay shoreline. Only ONE roofing contractor is physically headquartered inside Leonardtown 20650 (a 47-review local pack regulator that holds the Knowledge Graph slot on the head term). The next-closest in-county roofers cluster 9 to 14 miles north in Hollywood and Mechanicsville (one with 149 Google reviews, several with 5-star 70 to 165 review counts), with the only HAAG-credentialed local-pack competitor sitting in California MD 7 miles southeast. JDH HQ is 22 miles north in St Leonard, MD via MD-235 and MD-4 (32 minutes door-to-door), well inside the operational range that lets us pack Leonardtown jobs alongside our daily California, Hollywood, and Lexington Park work, but JDH's 1,400+ total reviews across all platforms (at 4.9 stars) dwarfs the ENTIRE 10-mile-radius competitor ring around Leonardtown combined (which collectively hold roughly 700 to 750 reviews across all named roofers). And critically, NONE of the in-market Leonardtown-orbital roofers stack HAAG Master plus OC Platinum plus James Hardie Elite plus ProVia Platinum. NONE have third-generation 1986 founding tenure. NONE position to the Leonardtown Historic District preservation-aware roofing market, the St. Mary's County seat institutional workforce, or the Breton Bay tidal Potomac tributary waterfront premium-spec mix specifically.
Three Generations · Family-Owned Since 1986
Founded in 1986 by Jim Dodson Sr., who built the company on federal-grade construction at the Pentagon and U.S. State Department, an origin story uniquely relevant to a Leonardtown county-seat institutional-workforce audience anchored by the St. Mary's County government, MedStar St. Mary's Hospital, the Leonardtown HS and Ryken HS school catchments, and the Pax River civilian-contractor commuter pool. His son Jim runs operations today as a HAAG Master Certified Inspector under cert #992109047, and the third generation, J.J., is age 4. The only Leonardtown-HQ roofer is a post-2015 operator with under 50 Google reviews; the nearest Hollywood and Mechanicsville competitors are 5-to-15-year operators; the only HAAG-credentialed California MD competitor is a 5-year operator with 82 reviews. NONE are third-generation family. The same family will answer your warranty phone in 2036.
The Only Stacked-Credential Contractor Working Leonardtown 20650
18 completed Leonardtown jobs inside the 20650 footprint with documented Owens Corning Duration installs (Driftwood, Aged Copper) across Clarks Rest, Society Hill, the Tudor Hall estate area, and the Breton Bay shoreline, packed alongside JDH's much larger sibling-city portfolios: 52 California MD jobs, 51 Lexington Park jobs, 34 Huntingtown jobs, plus deep concentrations across Hollywood, Mechanicsville, Charlotte Hall, and the rest of the St. Mary's County footprint. JDH's 1,400+ total reviews at 4.9 stars across all platforms dwarfs the ENTIRE 10-mile competitor ring around Leonardtown combined (roughly 700 to 750 reviews across all named in-county roofers). Material delivery and labor pool aligned: Beacon Lexington Park (~25 min south), ABC Supply Waldorf (~45 min west), SRS Distribution Lexington Park branches. Crews packed alongside daily California and Lexington Park work from St Leonard HQ (~32 min north via MD-235 and MD-4).
HAAG Master Certified Inspections + Maryland MHIC #137491
HAAG Engineering is the forensic standard insurance adjusters use to assess roof damage, and it is also the diagnostic standard the St. Mary's County Historic Preservation Commission recognizes for complex historic-roof systems including standing-seam metal and cedar on heritage buildings. Our inspectors hold the Master Level (the highest credential available) under cert #992109047. When we document a Leonardtown storm claim including the May 22, 2025 hail event that hit Leonardtown plus the August 4, 2020 Tropical Storm Isaias EF-1 tornado near Leonardtown plus Hurricane Isabel September 18, 2003 Breton Bay tidal flooding, your State Farm, USAA, Allstate, Liberty Mutual, or Travelers carrier sees the photos and scope of loss in the format their own adjuster produces. JDH carries Maryland MHIC #137491, the only credential that matters for MD homeowners compliance verification on a St. Mary's County DLU and GM building permit (the permit office physically inside Leonardtown at 23150 Leonard Hall Drive). Of the 10-mile-radius competitor ring around Leonardtown, only ONE competitor (a California MD operator) displays a HAAG certification number, NONE stack HAAG Master plus OC Platinum plus James Hardie Elite plus ProVia Platinum, and NONE position credibly to the Leonardtown Historic District preservation-aware roofing market on a 1660-founded town.
Fixed Pricing, Written Before Tear-Off
Our written quote is the final price. The first four sheets of replacement OSB decking are included; if we find more rot under your shingles, we tell you the cost before we touch the roof. We assume the risk, not you. That is the entire reason we hold a 4.9-star average across 1,400-plus reviews, and it is the entire reason the Leonardtown county-government-employee household, the MedStar St. Mary's Hospital nurse pre-listing household, the Clarks Rest or Society Hill multi-decade-tenure combo project, the Breton Bay waterfront homeowner authorizing a coastal-rated upgrade, or the downtown Leonardtown Historic District homeowner authorizing a preservation-aware standing-seam metal or cedar replacement trusts us with the kind of one-shot capital decision the next 30 years rest on. National franchise roofers lead with "Nation's Largest Platinum Roofer" and lifetime warranties; we lead with "no add-ons after tear-off" and a transferable manufacturer warranty.
State License (MD)
- MHIC #137491
- St. Mary's County DLU and GM Permit Compliant
- Maryland Building Performance Standards
Manufacturer Partnerships
- Owens Corning Platinum Preferred
- ProVia Platinum Dealer
- VELUX Certified Installer
- James Hardie Elite Preferred
Awards & Accreditations
- HAAG Master Certified Inspector #992109047
- BBB A+ Accredited
- Qualified Remodeler HIP 200
- GuildQuality Guildmaster
Recent Leonardtown MD Work
Two representative jobs from the Leonardtown housing-stock pattern. The first: a Clarks Rest 2-story colonial reroof on a first-replacement-cycle home in the eastern-edge planned-subdivision wave, county-government-employee household running a weekend install ahead of a pre-listing window. HAAG inspection on a Monday, install Friday-Saturday, listing photos the following week. The second: a Breton Bay-area waterfront-adjacent home storm-damage insurance-claim replacement after the May 22, 2025 hail event impact with carrier claim processing inside 14 days.
What Our Leonardtown MD Customers Say
Three representative examples from Leonardtown, MD homeowners across Clarks Rest, the Breton Bay area, and the downtown historic district. See all 1,400+ reviews on Google.
"JDH replaced the roof on our Clarks Rest 2-story colonial right before my pre-listing window. HAAG inspection on a Monday, install Friday-Saturday, listing photos the next week. Color-matched our neighbor's Owens Corning Duration Driftwood exactly. MHIC number was right on the quote, which mattered for our buyer's mortgage. Best contractor experience we have had in St. Mary's County."
"County-government household with a long-tenure tie to Leonardtown. JDH scheduled a Saturday install on our Society Hill 2-story so we did not have to burn a weekday off the courthouse calendar. Roof and gutters done in one visit. Quote was the final price. Best contractor experience we have had in 20650, and the permit was filed right at the DLU and GM office a mile from our house."
"Carrier claim after the May 22, 2025 hail event hit our Breton Bay area home. JDH walked our adjuster through the damage with HAAG documentation, claim approved in 14 days. Class 4 impact-rated SureNail install done in 2 days in Owens Corning Duration Aged Copper. We have looked at every Leonardtown-area roofer and none of them stack HAAG plus OC Platinum plus James Hardie Elite plus ProVia Platinum the way JDH does."
Neighborhoods & ZIP Codes We Serve in Leonardtown, MD
Leonardtown, MD is the only incorporated town in St. Mary's County, covering primary ZIP 20650 inside the town limits, with the USPS-shared adjacent ZIPs of 20627 Compton, 20624 Clements, 20618 Bushwood, and 20653 Park Hall (the latter shared with Lexington Park) all routinely co-marketed with Leonardtown for the Southern MD home-improvement supplier-account route. The Leonardtown Historic District in the downtown 20650 core is the largest single architectural-heritage identity driver in the town, with Leonardtown Wharf (the May 2008 waterfront park on Breton Bay and gateway to the McIntosh Run paddle trail), the Tudor Hall estate area (Georgian brick 1798, now St. Mary's County Historical Society headquarters), the Breton Bay shoreline (including the Breton Bay country club community on the south side), Clarks Rest (the large post-2010 planned subdivision on the eastern edge along MD-5), Society Hill, and the Leonardtown Square downtown commercial district (First Friday arts events, Wednesday farmers market, Port of Leonardtown Winery, restored historic restaurant cluster) rounding out the town-limit neighborhoods. We work all of it from Southern MD supplier accounts at Beacon Lexington Park (~25 min south via MD-5), ABC Supply Waldorf (~45 min west via MD-5 then MD-228), and SRS Distribution Lexington Park, with one crew standard, one warranty, one Maryland MHIC #137491, and one fixed-price model whether you are in a Clarks Rest 2010s 2-story colonial, a Society Hill or Tudor Hall area home, a Compton 20627 or Clements 20624 rural-residential parcel, a Breton Bay waterfront-adjacent home, or a downtown Leonardtown Historic District heritage building inside Historic Preservation Commission scope.
Leonardtown MD Neighborhoods
JDH also serves the rest of St. Mary's County from St Leonard HQ. Tap a sibling city for a dedicated page, or go up to the St. Mary's County hub.
Leonardtown MD Roofing & Exterior Questions
What is the average cost of a new roof in Leonardtown, MD?+
What is the 25% rule for roofing in Leonardtown, MD?+
What is the cheapest time of year to get a new roof in Leonardtown, MD?+
Do I need a permit to replace my roof in Leonardtown, MD?+
Does my Leonardtown home need historic-preservation review to replace the roof?+
Can JDH install standing-seam metal or cedar shake on historic district homes in downtown Leonardtown?+
Are roofs on Breton Bay waterfront homes treated differently than inland Leonardtown roofs?+
Why is Leonardtown housing stock different from California MD or Lexington Park?+
Does JDH service the Breton Bay country club community and Clarks Rest subdivisions in addition to the downtown historic district?+
Are Compton, Clements, Bushwood, and Park Hall homes considered part of Leonardtown for roofing service?+
Did the May 22, 2025 hail event hit Leonardtown roofs?+
How long does a roof replacement take in Leonardtown, MD for a typical Clarks Rest or Society Hill 2-story colonial?+
Free Leonardtown MD Home InspectionNo Pressure. No Pitch. Just the truth.
A HAAG Master Certified inspector will walk your Leonardtown, MD home (roof, siding, windows, doors, gutters), photograph every area of concern, and email you a written report within 24 hours. Same-day inspection most days. Early-morning, evening, and Saturday slots available across the downtown Leonardtown Historic District, Clarks Rest, Society Hill, the Tudor Hall area, the Breton Bay shoreline including the Breton Bay country club community, the Leonardtown Wharf, plus the USPS-shared Compton 20627, Clements 20624, Bushwood 20618, and Park Hall 20653 ring. Built for the St. Mary's County seat institutional-workforce household, the MedStar St. Mary's Hospital or Leonardtown HS or Ryken HS pre-listing window, and the St. Mary's County Historic Preservation Commission preservation-aware roofing scope. Maryland MHIC #137491.
- Full exterior inspection across all trades
- Photo report emailed within 24 hours
- State Farm / USAA / Allstate / Liberty Mutual claim documentation
- Fixed-price written quote, no add-ons
- Manufacturer warranties up to 50 years
Request Received
A real person from JDH Remodeling will follow up shortly.
- Within minutes: confirmation email and text
- Same day: a call to confirm a time that works
- On site: 60-to-90 minute forensic inspection with full photo report