Get matched with top roofers in Chestertown, MD
Enter your zip and get matched with up to 5 pros
Need a pro for your roofing project in Chestertown, MD?
Select your specific project to find the pro for you.
TRUSTED BY CHESTERTOWN, MD HOMEOWNERS
4.2 Average homeowner rating
189 Verified roofing services reviews
Verified Reviews for Roofing pros in Chestertown, MD
*The Angi rating for Roofing companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
*The HomeAdvisor rating for Roofing companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
Last update on January 01, 2026
Find Roofers in Chestertown
Home Genius Exteriors
Home Genius Exteriors
Super Service Award
Customers say: True professional
22 years of experience
Free onsite estimate
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"Perfect from start to finish"
Debbie B on December 2025
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"Perfect from start to finish"
Debbie B on December 2025
Home Genius Exteriors
Home Genius Exteriors
Super Service Award
Customers say: Super punctual
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
8 years of experience
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"The crew was friendly, courteous and professional. They showed up on time and got the work done in one day! I am impressed with the job done! And want to give thanks to Angel Martinez our project manager, he was amazing and always available for any questions and concerns I had! I want to thank Home Genius for a job well done!"
Mathew P on December 2025
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"The crew was friendly, courteous and professional. They showed up on time and got the work done in one day! I am impressed with the job done! And want to give thanks to Angel Martinez our project manager, he was amazing and always available for any questions and concerns I had! I want to thank Home Genius for a job well done!"
Mathew P on December 2025
Home Genius Exteriors
Home Genius Exteriors
Customers say: Super punctual
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
22 years of experience
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"They did a good job and took their time to do it right."
Dominic A on October 2025
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"They did a good job and took their time to do it right."
Dominic A on October 2025
Home Genius Exteriors
Home Genius Exteriors
Customers say: Quality work
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
22 years of experience
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"Everyone was amazing, workers and crew were efficient, cleanliness was great and we recommend them for all projects. Thank you Ty, AJ and Bryan for an great experience!"
charles n on December 2024
Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!
"Everyone was amazing, workers and crew were efficient, cleanliness was great and we recommend them for all projects. Thank you Ty, AJ and Bryan for an great experience!"
charles n on December 2024
Certified Roofing
Certified Roofing
Super Service Award
Customers say: Quality work
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
42 years of experience
Certified is a family-owned business, after leaving a decorated career as a Navy SEAL, Steve entered the trades of Commercial Roofing, and Residential Roofing for 1 reason: he loved the satisfaction of solving people's roof problems. Customers love us because of our Military and First Responder Discounts, plus our 100% custom satisfaction rate. We also have industry affiliations and certifications such as CertainTeed 5-Star, CSSB and Mule-Hide. Our estimates and visits are always free. Certified offers Commercial and Residential contracting services in Maryland, Washington DC, Virginia, West Virginia, and Delaware.
"I had a small leak in my roof next to a vent pipe. repairman was prompt and courteous. price was better than others. I would definitely hire them again if needed."
Ed S on December 2025
Certified is a family-owned business, after leaving a decorated career as a Navy SEAL, Steve entered the trades of Commercial Roofing, and Residential Roofing for 1 reason: he loved the satisfaction of solving people's roof problems. Customers love us because of our Military and First Responder Discounts, plus our 100% custom satisfaction rate. We also have industry affiliations and certifications such as CertainTeed 5-Star, CSSB and Mule-Hide. Our estimates and visits are always free. Certified offers Commercial and Residential contracting services in Maryland, Washington DC, Virginia, West Virginia, and Delaware.
"I had a small leak in my roof next to a vent pipe. repairman was prompt and courteous. price was better than others. I would definitely hire them again if needed."
Ed S on December 2025
CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
Customers say: Quality work
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
39 years of experience
Looking for top-notch roofing, windows, and siding services in Maryland? Look no further than CHESAPEAKE ROOFING WINDOWS & SIDING. With our MHIC LICENSE #126792, we deliver exceptional craftsmanship and customer satisfaction. Contact us today for all your home improvement needs!
"David and his window installation team are incredibly hard working and professional. They have a strong commitment to excellence and work diligently to ensure everything is done well. David answers questions and explains options thoroughly. We would definitely do business with Chesapeake Roofing in the future based on our experience."
Nancy M on April 2023
Looking for top-notch roofing, windows, and siding services in Maryland? Look no further than CHESAPEAKE ROOFING WINDOWS & SIDING. With our MHIC LICENSE #126792, we deliver exceptional craftsmanship and customer satisfaction. Contact us today for all your home improvement needs!
"David and his window installation team are incredibly hard working and professional. They have a strong commitment to excellence and work diligently to ensure everything is done well. David answers questions and explains options thoroughly. We would definitely do business with Chesapeake Roofing in the future based on our experience."
Nancy M on April 2023
Tar Heel Construction Group, LLC
Tar Heel Construction Group, LLC
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
22 years of experience
As a roofing company serving Bel Air, Maryland since 2004 our goal is simple. We will exceed our customers' roofing expectations with quality roofing work and craftsmanship every time. By building relationships, through the home improvement process, customers' are given a home to be proud of, a roofing company that they trust, and the peace of mind knowing that we stand behind 100% of our work 100% of the time. Since its conception Tar Heel Construction Group, LLC has focused on three core business principles: accountability, roofing job quality, and customer satisfaction. Click here to view our roofing service locations in the Greater Baltimore region!
"Courteous and professional recent roof and gutter replacement. Thorough presentation of product by Brian, hard working crew, and good supervision of task from beginning to completion by Ryan and Brian. Attention given to each of my questions and concerns. Good phone communication for time schedules, arrivals, changes, etc."
Karen T on April 2020
As a roofing company serving Bel Air, Maryland since 2004 our goal is simple. We will exceed our customers' roofing expectations with quality roofing work and craftsmanship every time. By building relationships, through the home improvement process, customers' are given a home to be proud of, a roofing company that they trust, and the peace of mind knowing that we stand behind 100% of our work 100% of the time. Since its conception Tar Heel Construction Group, LLC has focused on three core business principles: accountability, roofing job quality, and customer satisfaction. Click here to view our roofing service locations in the Greater Baltimore region!
"Courteous and professional recent roof and gutter replacement. Thorough presentation of product by Brian, hard working crew, and good supervision of task from beginning to completion by Ryan and Brian. Attention given to each of my questions and concerns. Good phone communication for time schedules, arrivals, changes, etc."
Karen T on April 2020
Castillo Construction
Castillo Construction
Super Service Award
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
12 years of experience
Castillo Construction is Maryland's premier roofing company. Our team is dedicated to getting your job done quickly and done well. We pride ourselves on our quality of work and our value. Call us today and see why your neighbors use Castillo Construction.
"Yes. Excellent "
Calaway M on March 2025
Castillo Construction is Maryland's premier roofing company. Our team is dedicated to getting your job done quickly and done well. We pride ourselves on our quality of work and our value. Call us today and see why your neighbors use Castillo Construction.
"Yes. Excellent "
Calaway M on March 2025
Canales Service, LLC
Canales Service, LLC
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
8 years of experience
We pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects no matter how big or small. We are experts in our trade and will always keep you educated on your particular task or project. We look forward to earning your business!
"Amazing company and very fast response. Will 100% use again when needed"
Kevin A on April 2025
We pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects no matter how big or small. We are experts in our trade and will always keep you educated on your particular task or project. We look forward to earning your business!
"Amazing company and very fast response. Will 100% use again when needed"
Kevin A on April 2025
AROCON Roofing & Construction
AROCON Roofing & Construction
Customers say: Super punctual
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
18 years of experience
AROCON offers superior services at an affordable price because we are your Maryland & Virginia contractor. We service all of Anne Arundel, Baltimore, Carroll, Dorchester, Frederick, Howard, Harford, Montgomery, Prince George's, Queen Annes, Talbot, Wicomico, and Worchester Maryland counties, as well as Fairfax, Arlington, Loudoun, Fauquier, and Prince William, Virginia counties and parts of Southern Pennsylvania. Instead of focusing on completing as many jobs as possible, AROCON focuses on providing quality work and getting to know our customers. This allows us to provide high quality, customized results and unparalleled customer service without adding extensive overhead or expenses. For all of your Roofing & Construction needs, you can count on our experienced team at AROCON Roofing & Construction. We service all of Anne Arundel, Baltimore, Carroll, Frederick, Howard, Harford and Montgomery counties, including parts of Prince George's county and Southern Pennsylvania. Call us today to make Home Improvement, Simplified. #rooftuneup.
"They quoted half of the other two we got quotes from. Work was scheduled a couple weeks later and done in a day."
Katrina B on October 2024
AROCON offers superior services at an affordable price because we are your Maryland & Virginia contractor. We service all of Anne Arundel, Baltimore, Carroll, Dorchester, Frederick, Howard, Harford, Montgomery, Prince George's, Queen Annes, Talbot, Wicomico, and Worchester Maryland counties, as well as Fairfax, Arlington, Loudoun, Fauquier, and Prince William, Virginia counties and parts of Southern Pennsylvania. Instead of focusing on completing as many jobs as possible, AROCON focuses on providing quality work and getting to know our customers. This allows us to provide high quality, customized results and unparalleled customer service without adding extensive overhead or expenses. For all of your Roofing & Construction needs, you can count on our experienced team at AROCON Roofing & Construction. We service all of Anne Arundel, Baltimore, Carroll, Frederick, Howard, Harford and Montgomery counties, including parts of Prince George's county and Southern Pennsylvania. Call us today to make Home Improvement, Simplified. #rooftuneup.
"They quoted half of the other two we got quotes from. Work was scheduled a couple weeks later and done in a day."
Katrina B on October 2024
Roofing questions, answered by experts
The Chestertown, MD homeowners’ guide to roofing services
From average costs to expert advice, get all the answers you need to get your job done.
Learn all of the factors you need to consider to estimate roof ridge cap replacement costs, whether it’s safe and worthwhile to DIY the work, and more.
Raising the roof on a Cape Cod house adds valuable living space. Learn how much it costs to raise the roof on a Cape Cod house and what affects the price.
Getting a wind mitigation inspection can work in your financial favor. Learn about the average wind mitigation inspection cost, including ways to save.
Wondering how to decide between the different types of roof shingles? Here's what you need to know about each and how to choose what's best for your home.
Know the different pros and cons of different types of asphalt shingles, including three-tab, architectural, and luxury shingles.
Discover how to install metal roofing over shingles to add long-lasting weather protection to your existing roof without removing the old material.
- Worton, MD Roofers
- Rock Hall, MD Roofers
- Kennedyville, MD Roofers
- Church Hill, MD Roofers
- Centreville, MD Roofers
- Sudlersville, MD Roofers
- Millington, MD Roofers
- Galena, MD Roofers
- Queenstown, MD Roofers
- Earleville, MD Roofers
- Henderson, MD Roofers
- Edgewood, MD Roofers
- Queen Anne, MD Roofers
- Perryman, MD Roofers
- Essex, MD Roofers
- Middle River, MD Roofers
- Cecilton, MD Roofers
- Grasonville, MD Roofers
- Riverside, MD Roofers
- Belcamp, MD Roofers
- Chester, MD Roofers
- Joppa, MD Roofers
- Goldsboro, MD Roofers
- White Marsh, MD Roofers
- Abingdon, MD Roofers
- Aberdeen, MD Roofers
- Marydel, DE Roofers
- Dundalk, MD Roofers
- Ridgely, MD Roofers
- Clayton, DE Roofers
- Siding
- Gutter Repair Replacement
- Skylights
- Chimney Repair
- Roof Cleaning
- Solar Panels
- Insulation
- Contractor
- Water And Smoke Damage
- Pole Barn Builders
- Tv Antenna Installation
- Chimney Sweep
- Treehouse Builders
- Patio Covers
- Hurricane Shutters
- Repair Carport
- Dumpster Rental
- Gutter Cleaning
- Chimney Liner Installation
- Animal Removal
- Sunroom And Patio Remodeling
What do you need done? We’ll find top pros.
- 🌱 "Mow a small front yard"
- 🛠 "Fix a leaking pipe under the sink"
- 🏠 "Repair shingles on an asphalt roof"