Best Roofing Companies Near You in Chestertown, MD (2026)
Top Roofers in Chestertown, MD
Filter by service:
Jones Asphalt, Maintenance & Construction LLC
Jones Asphalt is known for punctual, professional service and quality workmanship that customers consistently praise. Reviewers highlight the team's expertise, personable communication throughout projects, and ability to deliver results efficiently—often completing jobs faster than estimated. Many customers appreciate their fair pricing, willingness to consult on options, and the passion they bring to getting work done right the first time.
"My wife and I just purchased our home and didn't want to spend an arm and a leg getting the old ribbon driveway re-paved. I called 4 separate companies and Jones Asphalt was the only company to actually come out, assess my driveway, and give a quote on the spot. Nick Jr. was very personable and honest. He has lots of knowledge about the asphalt business. His passion for the business and doing things right the first time really shine through with…" — Eric J.
+1 301-250-6906
Customers consistently praise this air duct cleaning company for their professionalism, punctuality, and friendly technicians who take time to explain their work and answer questions thoroughly. The team is known for delivering exceptional results—documented with before-and-after photos—while being honest about pricing and avoiding high-pressure upselling tactics. Clients appreciate their reliable service in the Kingsville area and their willingness to address urgent issues like blocked dryer vents that impact home air quality and health.
"josiah, ruben, and edward did a fantastic job cleaning out my air ducts. josiah explained each step of the process and shared how this would really help improve my sinus and asthma problems. all three were friendly, arrived on time, and even offered some helpful tips about keeping my vents cleaner in the future. i was amazed by how much dust and debris they removed from the ducts—it made a huge difference in my home’s air quality. now, even my…" — Beverly H.
+1 410-220-0013
Bel Air Roofing & Siding is praised by customers for reliable, high-quality work completed on schedule with reasonable pricing that often beats competitor quotes. Clients consistently highlight the professionalism and responsiveness of the team, including owner Todd's personal involvement in projects and accessibility for questions throughout the job. The company earns recognition for meticulous cleanup, respect for customers' properties and neighborhoods, and genuine customer service that keeps clients returning for future projects and recommending them to others.
"We couldn’t be happier with the service we received from Bel Air Roofing & Siding! From the very first phone call to the final walk-through, the communication was clear and professional. The crew showed up on time, worked efficiently, and treated our property with care and respect. Not only did they do excellent work on both our roofing and siding repairs, but they also beat every other quote we received — by far. It’s rare these days to find…" — Kristina K.
+1 443-371-6948
Why Hire a Local Roofer in Chestertown?
Local Climate Knowledge
Chestertown roofers understand Maryland's specific weather patterns and choose materials built to last in local conditions.
Building Code Compliance
Local contractors know Chestertown's permit requirements and code standards, ensuring your repair passes inspection.
Faster Response Times
A local company can respond to emergencies quickly and follow up easily if issues arise after the repair.
Typical Roof Repair Costs in Chestertown
| Repair Type | Typical Cost Range |
|---|---|
| Minor Leak Repair | $150 – $400 |
| Shingle Replacement (small area) | $300 – $900 |
| Flashing Repair | $200 – $600 |
| Gutter Repair / Replacement | $150 – $500 |
| Section Repair (large area) | $1,500 – $5,000 |
| Emergency Repair | $500 – $1,500 |
| Full Roof Replacement | $8,000 – $25,000+ |
* Estimates only. Actual costs vary by scope, materials, and contractor. Get at least 3 quotes.
FAQ: Roof Repair in Chestertown, MD
Roof repair costs in Chestertown typically range from $150–$400 for minor leak repairs to $1,500–$5,000 for extensive section repairs. Emergency repairs can cost more. The exact price depends on the extent of damage, roofing material, roof pitch, and the contractor you choose. Always get 3 quotes before committing.
Find Roofers in Other Maryland Cities
Top-rated contractors near Chestertown, organized by city