Top-rated roofers.

Get matched with top roofers in Chestertown, MD

There are 17 highly-rated local roofers.

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

Average homeowner rating star icon4.2
Average homeowner rating
Verified reviews icon195
Verified roofing services reviews

Roofers in Chestertown

Avatar for AROCON Eastern Shore
AROCON Eastern Shore
301 Crusader Rd
4.67(
12
)
Approved Pro
AROCON Eastern Shore
301 Crusader Rd
4.67(
12
)
Approved Pro
Customers say: Quality work
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
192 local quotes requested

AROCON Roofing & Construction offers superior services at an affordable price because we are your Maryland contractor. 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 Dorchester, Queen Annes, Talbot, Wicomico, and Worchester counties. Call us today to make Home Improvement, Simplified. #rooftuneup.

"Great contractor. Very friendly and professional."

Richard G on July 2024

AROCON Roofing & Construction offers superior services at an affordable price because we are your Maryland contractor. 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 Dorchester, Queen Annes, Talbot, Wicomico, and Worchester counties. Call us today to make Home Improvement, Simplified. #rooftuneup.

"Great contractor. Very friendly and professional."

Richard G on July 2024


Avatar for Innovative Home Improvement
Innovative Home Improvement
6533 Meadowfield Ct
5.00(
119
)
Approved Pro
Innovative Home Improvement
6533 Meadowfield Ct
5.00(
119
)
Approved Pro
Customers say: True professional
Recommended by 99% of Angi customers
Recommended by 99% of HomeAdvisor customers
72 local quotes requested

We are a family owned and operated company since 1986. .We are a client based company,hassle free no sales pressure or gimmicks with our presentations.we offer one of the best warranties in the market .We have our own crews to guarantee great installations every time.We offer premier energy efficient vinyl windows and vinyl siding.

"Responsive, responsible and did all that was promised. Promply corrected small mistake."

Judith R on June 2025

We are a family owned and operated company since 1986. .We are a client based company,hassle free no sales pressure or gimmicks with our presentations.we offer one of the best warranties in the market .We have our own crews to guarantee great installations every time.We offer premier energy efficient vinyl windows and vinyl siding.

"Responsive, responsible and did all that was promised. Promply corrected small mistake."

Judith R on June 2025


Avatar for Roofing Pups, Roofing & Siding - MD
Roofing Pups, Roofing & Siding - MD
7855 Belair Rd
4.55(
44
)
Approved Pro
Roofing Pups, Roofing & Siding - MD
7855 Belair Rd
4.55(
44
)
Approved Pro
Customers say: Quality work
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
344 local quotes requested

Since 1992, Roofing Pups, Roofing & Siding - MD has provided homeowners and business owners with top quality, factory-direct products, professionally installed by licensed, bonded installers with over 25 years of home improvement experience. Our experience sales representative will assist you with the windows and/or doors that suit you best. Roofing Pups Roofing & Siding takes pride in building relationships with not only our consumers but with our manufacturers as well. We have maintained a reputable business relationship with both of our leading manufactures, American Jewel and Home Guard, for 15 years. Being a locally owned and operated company, Roofing Pups is able to provide you with top quality products with a bottom line price! Come see for yourself how Air Tite Windows & Doors, Inc. can make your home look stunning and more energy efficient.

"Great.good job"

Linwood C on May 2025

Since 1992, Roofing Pups, Roofing & Siding - MD has provided homeowners and business owners with top quality, factory-direct products, professionally installed by licensed, bonded installers with over 25 years of home improvement experience. Our experience sales representative will assist you with the windows and/or doors that suit you best. Roofing Pups Roofing & Siding takes pride in building relationships with not only our consumers but with our manufacturers as well. We have maintained a reputable business relationship with both of our leading manufactures, American Jewel and Home Guard, for 15 years. Being a locally owned and operated company, Roofing Pups is able to provide you with top quality products with a bottom line price! Come see for yourself how Air Tite Windows & Doors, Inc. can make your home look stunning and more energy efficient.

"Great.good job"

Linwood C on May 2025


Avatar for Home Genius Exteriors
Home Genius Exteriors
8201 Corporate Dr.
4.86(
258
)
Approved Pro
Home Genius Exteriors
8201 Corporate Dr.
4.86(
258
)
Approved Pro
Customers say: Super punctual
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
905 local quotes requested

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 whole crew did a magnificent job on my siding project. I'm a little disappointed in hindsight that I chose not to go with new soffit as well, but that's going to be my next steps! Thanks again to the whole team and am looking forward to having you all back in the near future. Highest regards from the Roseman household!"

Beatrice R on August 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 whole crew did a magnificent job on my siding project. I'm a little disappointed in hindsight that I chose not to go with new soffit as well, but that's going to be my next steps! Thanks again to the whole team and am looking forward to having you all back in the near future. Highest regards from the Roseman household!"

Beatrice R on August 2025


Avatar for Certified Roofing
Certified Roofing
9520 Berger Rd Suite 112
4.82(
885
)
Approved Pro
Certified Roofing
9520 Berger Rd Suite 112
4.82(
885
)
Approved Pro
Customers say: Quality work
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
283 local quotes requested

Conveniently located in Columbia, Maryland, and Vienna, Virginia. Locally family and veteran owned & operated. Award winning. For the past 40 years, Certified has offered the Maryland, Washington DC, Northern Virginia, Hampton Roads, and Delaware, areas the highest quality workmanship and unmatched level of expertise in specialty metal, shingle, slate, cedar shake, and flat roofing installation. Certified is known for its skilled craftsmen and their attention to detail. All of the professional roofers, estimators, and project managers have completed thousands of hours of training from the largest manufacturers of roofing products. We strive for 100% satisfaction. The training and certifications we earned allow us to live up to this goal. We are confident we will far exceed your expectations on your next roofing, siding, window, or gutter project. Although we have completed many large commercial, industrial, religious and educational projects, the majority of our work is the installation of replacement roofs on residential homes. Licensed in MD, DC, DE, and VA.

"Great! Sales person walked me through the entire process and showed me a sample of all the products they use, including the warranty. The total cost came in under the estimate!"

Lou F on August 2025

Conveniently located in Columbia, Maryland, and Vienna, Virginia. Locally family and veteran owned & operated. Award winning. For the past 40 years, Certified has offered the Maryland, Washington DC, Northern Virginia, Hampton Roads, and Delaware, areas the highest quality workmanship and unmatched level of expertise in specialty metal, shingle, slate, cedar shake, and flat roofing installation. Certified is known for its skilled craftsmen and their attention to detail. All of the professional roofers, estimators, and project managers have completed thousands of hours of training from the largest manufacturers of roofing products. We strive for 100% satisfaction. The training and certifications we earned allow us to live up to this goal. We are confident we will far exceed your expectations on your next roofing, siding, window, or gutter project. Although we have completed many large commercial, industrial, religious and educational projects, the majority of our work is the installation of replacement roofs on residential homes. Licensed in MD, DC, DE, and VA.

"Great! Sales person walked me through the entire process and showed me a sample of all the products they use, including the warranty. The total cost came in under the estimate!"

Lou F on August 2025


Avatar for Exquisite Roofing & Exteriors, LLC
Exquisite Roofing & Exteriors, LLC
216 NAJOLES RD
4.67(
12
)
Approved Pro
Exquisite Roofing & Exteriors, LLC
216 NAJOLES RD
4.67(
12
)
Approved Pro
Customers say: Quick response
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
84 local quotes requested

Exquisite Roofing and Exteriors LLC is a family owned and operated business that's fully committed to serving the residential roofing, windows, and other interior/exterior home improvement needs of our clients. We pride ourselves on quality and professionalism. In addition to residential and commercial roofing services, we also specialize in providing a broad range of services including window replacements, storm damage repair, metal roofing, custom deck design, replacement of doors, gutter replacement services, and more! We are CertainTeed preferred contractors and GAF certified! We are fully licensed and certified to operate with your insurance! and Yes we do provide FREE No-Obligation Estimates! ALL ESTIMATES ARE GOOD FOR 90 days Give us a call, message, or email! [email protected] Office manager phone: (443)734-7152 We also have the app so message us too if that is more convenient for you!

"No show for an in-person estimate after I spoke with someone on the phone."

Peter R on June 2024

Exquisite Roofing and Exteriors LLC is a family owned and operated business that's fully committed to serving the residential roofing, windows, and other interior/exterior home improvement needs of our clients. We pride ourselves on quality and professionalism. In addition to residential and commercial roofing services, we also specialize in providing a broad range of services including window replacements, storm damage repair, metal roofing, custom deck design, replacement of doors, gutter replacement services, and more! We are CertainTeed preferred contractors and GAF certified! We are fully licensed and certified to operate with your insurance! and Yes we do provide FREE No-Obligation Estimates! ALL ESTIMATES ARE GOOD FOR 90 days Give us a call, message, or email! [email protected] Office manager phone: (443)734-7152 We also have the app so message us too if that is more convenient for you!

"No show for an in-person estimate after I spoke with someone on the phone."

Peter R on June 2024


Avatar for David N Donahue Siding & Windows
David N Donahue Siding & Windows
315 S Main St
4.69(
75
)
Approved Pro
David N Donahue Siding & Windows
315 S Main St
4.69(
75
)
Approved Pro
Customers say: Quality work
15 local quotes requested
50 years of experience

Angie’s List Super Service Award Winner!!! D. N. Donahue is your full-service Siding and Window contractor. With 40 years’ experience in the industry we know how to do the job right. We keep it simple, price efficient, and stand by our work. We also offer a lifetime warranty. You can rest easy, knowing that we will keep the job site clean, with the employees having many years of experience, including American Veterans. Call or message us today

"Excellent work,siding repaired quickly and professionally.Cost was also reasonable.Would highly recommend.Repairs are as good as new."

Gary L on May 2025

Angie’s List Super Service Award Winner!!! D. N. Donahue is your full-service Siding and Window contractor. With 40 years’ experience in the industry we know how to do the job right. We keep it simple, price efficient, and stand by our work. We also offer a lifetime warranty. You can rest easy, knowing that we will keep the job site clean, with the employees having many years of experience, including American Veterans. Call or message us today

"Excellent work,siding repaired quickly and professionally.Cost was also reasonable.Would highly recommend.Repairs are as good as new."

Gary L on May 2025


Avatar for Power Home Remodeling
Power Home Remodeling
2501 Seaport Dr
4.22(
1,048
)
Approved Pro
Power Home Remodeling
2501 Seaport Dr
4.22(
1,048
)
Approved Pro
Customers say: Quality work
269 local quotes requested
33 years of experience

As the nation’s largest full-service exterior home remodeler, we are backed by over 1,000+ Angi Super Service awards and more than one million happy customers. Why? Because we treat each job as an audition. An opportunity to prove ourselves to you. And the results speak for themselves. So make your home all it was meant to be with our unrivaled exterior services. Contact us today for a free, no obligation estimate on replacement windows, roofing, siding, doors, or attic insulation.

"Had Power replace all of our (9 - mostly custom size) windows in Florida with the Fortress Pella line. From sale - post install the entire process has been smooth. They actually installed our windows early - Customer service has been fantastic! Install and quality of windows is top notch. Haven’t had to worry about a thing. Would highly recommend (and I’m picky)!! Never felt pressured, answered my many detailed questions in sale and along the way, finishing work was done well, clean up was good and the crew had respect of our property and plants. Crew showed up around 9 and was done by 3:30. Great financing options and policy (no down payment, don’t have to pay till 60 days after successful install, no prepayment penalty, decent rate)!"

Taylor B on July 2025

As the nation’s largest full-service exterior home remodeler, we are backed by over 1,000+ Angi Super Service awards and more than one million happy customers. Why? Because we treat each job as an audition. An opportunity to prove ourselves to you. And the results speak for themselves. So make your home all it was meant to be with our unrivaled exterior services. Contact us today for a free, no obligation estimate on replacement windows, roofing, siding, doors, or attic insulation.

"Had Power replace all of our (9 - mostly custom size) windows in Florida with the Fortress Pella line. From sale - post install the entire process has been smooth. They actually installed our windows early - Customer service has been fantastic! Install and quality of windows is top notch. Haven’t had to worry about a thing. Would highly recommend (and I’m picky)!! Never felt pressured, answered my many detailed questions in sale and along the way, finishing work was done well, clean up was good and the crew had respect of our property and plants. Crew showed up around 9 and was done by 3:30. Great financing options and policy (no down payment, don’t have to pay till 60 days after successful install, no prepayment penalty, decent rate)!"

Taylor B on July 2025


Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
32221 Beaver Run Dr
4.60(
73
)
Approved Pro
Spicer Bros. Construction Inc.
32221 Beaver Run Dr
4.60(
73
)
Approved Pro
Customers say: Quality work
128 local quotes requested
23 years of experience

With over 20 years of experience, Spicer Bros. Construction is proud to provide exterior home remodeling services to Delmarva, as well as top-notch bathroom remodeling with our Baths By Spicer Bros. division. Our experienced and friendly staff will help you every step of the way, from the first phone call to the completion of your project. We strive to provide you with the highest level of customer service, fair pricing, and workmanship every single time. Look no further for any of your exterior renovations and bathroom remodeling needs!

"Never heard from them"

Fern B on June 2019

With over 20 years of experience, Spicer Bros. Construction is proud to provide exterior home remodeling services to Delmarva, as well as top-notch bathroom remodeling with our Baths By Spicer Bros. division. Our experienced and friendly staff will help you every step of the way, from the first phone call to the completion of your project. We strive to provide you with the highest level of customer service, fair pricing, and workmanship every single time. Look no further for any of your exterior renovations and bathroom remodeling needs!

"Never heard from them"

Fern B on June 2019


Avatar for CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
910 Soaring Eagle Court
4.85(
102
)
Approved Pro
CHESAPEAKE ROOFING WINDOWS & SIDING
910 Soaring Eagle Court
4.85(
102
)
Approved Pro
Customers say: Quality work
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
26 local quotes requested

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

...
Showing 1-10 of 216

FAQs for roofing projects in Chestertown, MD

Typical roofing repairs cost between $380 and $1,800 on average. However, most homeowners spend approximately $1,100 on a roofing repair project. The size of the roof, the extent of the damage, and the type of project all impact the final cost. External factors like product availability and supply chain issues may also affect the price. 

Projects like repairing damaged gutters will only be around $180 to $560, whereas repairing a sagging roof will be a higher expense at $1,500 to $7,000

Roofing is a highly skilled and labor-intensive trade. Because of this, you can expect to pay an average of $2 per square foot for your roofing professional. Roofing labor costs generally make up about 60% of the overall project cost. 

The cost to replace your roof is often significantly more expensive than the cost to repair it. On average, homeowners will spend between $5,890 and $12,800 to replace a roof. The size of the roof, the roof’s pitch, and the number of stories the house has will significantly affect the overall cost. You can expect to spend upwards of $46,000 for large, high-end roofs. 

Yes, most states require roofers to be licensed, and for good reason. Hiring an unlicensed roofer could lead to poor quality work, costly future expenses, and potential code violations.

As you browse our pro listings, take note of the “Angi Approved” badge. Angi Approved businesses meet our standards for certification which include:

  • The owner, principal, or relevant manager passed a criminal background check

  • Required to have applicable state and local licenses

  • Maintain an average star rating of 3.0 or better on our network, if they have at least one review

  • Paying to advertise their services

  • Meeting any other eligibility criteria required by Angi

Keep in mind licensing is different from certifications. A license is a legal requirement to operate a business, while certifications are voluntary.

Before hiring a roofing contractor to work on your project, there are a few things you will want to ask, including: 

  • Do you use roofing subcontractors?

  • Do you offer a warranty?

  • Do you have any references?

  • How will you clean up after the project is complete? 

  • Will you remove my old or damaged roof?

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.
Roof repairman fixing a tile roof
Jul 11, 2025
Jul 11, 2025
The average cost of roof repair for U.S. homeowners averages between $386 and $1,875. Learn what factors can affect roof repair costs.
view of house with tan siding, stone accents, and brown metal roof
Jul 10, 2025
Jul 10, 2025
A new metal roof can add a unique touch to your home’s curb appeal and help maximize efficiency. Learn about metal roof costs and what affects your total.
Tarp on a part of a roof
Mar 6, 2025
Mar 6, 2025
Wondering about the cost to tarp a roof after a large storm or before a major roof renovation? We'll break it down by size, style, and scenario.
A modern suburban house
Mar 24, 2025
Mar 24, 2025
Adding a layer of shingles to your roof may lead to big problems. Learn why there’s a limit to how many layers of shingles are allowed on a roof.
Young mother playing with two sons in front of house
Mar 7, 2025
Mar 7, 2025
From asphalt to clay tiles, how long does a roof last? Let's walk through the average roof lifespan based on materials, climate, ventilation, and more.
Roof top in traditional style
Mar 7, 2025
Mar 7, 2025
Comparing a tin roof vs. shingles for your home's best protection? Here's what you need to know about each material to make the right choice.