#1 Rated Roofing Contractor in St. Mary's County, MD

Roofing, Siding, Gutters, Windows and Doors serving St. Mary’s County and all of St. Mary’s County since 2010. GAF Master Elite Certified. MHIC #162131.

St. Mary's County Trusted Roofing and Exterior Contractor

St. Mary’s County is the southernmost county in Southern Maryland and one of the most historically rich communities in the state. Crossroads Contracting LLC serves homeowners throughout St. Mary’s County including Leonardtown, California, Lexington Park, Great Mills, Hollywood, and surrounding communities. We make the drive south regularly for roofing, siding, gutter, window, and door projects and treat every St. Mary’s County job with the same care and quality standard we bring to our home county.

St. Mary’s County homes face similar coastal Maryland challenges including Bay and Potomac River humidity, seasonal storm exposure, and the freeze-thaw cycles that stress roofing systems in winter. Leonardtown and the surrounding communities have a mix of older historic homes and newer construction subdivisions, and we have the experience to work on all of them.

Our Services in St. Mary's County, MD

Roof Installation and Replacement

We install GAF, CertainTeed, and Owens Corning roofing systems throughout St. Mary’s County. As a GAF Master Elite Certified contractor we offer the GAF Golden Pledge warranty covering both materials and labor for up to 25 years.

Learn More

Roof Repair

From storm damage to aging shingles, our roof repair team responds quickly to protect St. Mary’s County homes from water intrusion and further damage. We service all roof types common to St. Mary’s County homes.

Learn More

Vinyl Siding Installation

We install premium vinyl siding rated for Maryland climate conditions, helping St. Mary’s County homeowners protect their homes and boost curb appeal at the same time.

Learn More

Seamless Gutter Installation

We custom-fabricate seamless aluminum gutters on-site and install gutter guard systems that keep debris out year-round, protecting St. Mary’s County foundations from water damage.

Learn More

Storm Damage Repair

We provide rapid storm damage assessment and repair for St. Mary’s County homeowners and work directly with insurance companies to document and process claims efficiently.

Learn More

Roof Inspections

Our comprehensive roof inspections give St. Mary’s County homeowners a detailed, honest assessment of every component from ridge cap and flashing to fascia, soffit, and decking.

Learn More

Window Replacement

We install energy-efficient replacement windows that cut heating and cooling costs for St. Mary’s County homeowners while improving appearance and resale value.

Learn More

Door Replacement

We install and replace entry doors, storm doors, and sliding patio doors throughout St. Mary’s County with options in fiberglass, steel, and wood.

Learn More

GAF Certified Roofing

As a GAF Master Elite Certified contractor we offer St. Mary’s County homeowners the industry’s strongest roofing warranty with 25-year coverage on materials and labor.

Learn More

Why St. Mary's County Homeowners Choose Crossroads Contracting

GAF Master Elite Certified. Fewer than 3 percent of roofing contractors in the US hold this certification. It is the gold standard for quality and professionalism in the roofing industry.
MHIC Licensed Number 162131. We are fully licensed by the Maryland Home Improvement Commission, protecting you on every job we complete throughout Maryland.
14 plus years of experience. Founded in 2010 by Connor Kretzing, we have completed thousands of exterior projects across Southern Maryland.
5-star rated with 22 Google reviews. Every review is from a real Maryland homeowner. Our reputation is built on honest work and clear communication.

We never subcontract. Your job is done by our own trained crew, not handed off to a third party. That is how we maintain quality on every project.
Insurance claim expertise. We work directly with insurance adjusters and know how to document storm damage to maximize your claim payout.
Financing available. We offer flexible financing options for qualified homeowners throughout Maryland.
Free estimates. We provide free, no-obligation estimates with honest assessments and no pressure tactics.

Common Questions from St. Mary's County Homeowners

Do you serve all of St. Mary’s County?

Yes. We serve all communities in St. Mary’s County including Leonardtown, California, Lexington Park, Great Mills, Hollywood, Mechanicsville, Chaptico, Ridge, and surrounding areas. Call us at (443) 219-7323 to schedule a free estimate.

How long does it take to get an estimate in St. Mary’s County?

We typically schedule estimates in St. Mary’s County within 3 to 5 business days. For storm damage emergencies we prioritize scheduling and can often get to you sooner. Call us directly for urgent situations.

Do you offer a warranty on roofing work in St. Mary’s County?

Yes. As a GAF Master Elite contractor we offer the GAF Golden Pledge warranty which covers both materials and labor for up to 25 years. This warranty is transferable when you sell your home, adding documented value to your property. We also offer standard workmanship warranties on all other exterior work including siding, gutters, windows, and doors.

How do I get started with Crossroads Contracting in St. Mary’s County?

Simply call us at (443) 219-7323 or use our online contact form. We respond within a few hours and can typically schedule an on-site inspection within a few business days. Our estimates are free, detailed, and come with no pressure or obligation.

Results You Can Trust.

Your message was sent!

Thank you! We'll be in touch soon.

Get a Free Estimate in St. Mary's County, MD

Ready to protect your St. Mary’s County home? Call us or fill out our contact form for a free, no-obligation estimate. We respond quickly and schedule inspections within a few business days.

(443) 219-7323

Crossroads Contracting LLC, 3747 6th Street, North Beach, MD 20714