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Find Wood or fiber cement siding installation or complete replacement pros in Chestertown

TDS Contractors

420 Jarman Avenue
New on HomeAdvisorNew on HomeAdvisor
•Approved Pro

TDS Contractors

420 Jarman Avenue
New on HomeAdvisorNew on HomeAdvisor
•Approved Pro
7 years of experience
Free onsite estimate

At TDS Contractors, our company is based on the belief that our customers' needs are of the utmost importance. Our team is committed to meeting those needs. We welcome the opportunity to earn your trust and deliver you the best service. No job is too big or too small for our experienced team. Call today for a quote.

At TDS Contractors, our company is based on the belief that our customers' needs are of the utmost importance. Our team is committed to meeting those needs. We welcome the opportunity to earn your trust and deliver you the best service. No job is too big or too small for our experienced team. Call today for a quote.

Avatar for Home Genius Exteriors

Home Genius Exteriors

8201 Corporate Drive, Suite G10
4.94(
354
)
•Approved Pro

Home Genius Exteriors

8201 Corporate Drive, Suite G10
4.94(
354
)
•Approved Pro
Super Service Award
Customers say: Super punctual
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
32 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!

"Just imaging solution"

Jack S on April 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!

"Just imaging solution"

Jack S on April 2025

Avatar for Roofing Pups, Roofing & Siding

Roofing Pups, Roofing & Siding

633 Keith Lane
4.91(
34
)
•Approved Pro

Roofing Pups, Roofing & Siding

633 Keith Lane
4.91(
34
)
•Approved Pro
Super Service Award
Customers say: True professional
895 local quotes requested
31 years of experience

Since 1994, Air Tite Exteriors has provided homeowners in Maryland and D.C with top quality, factory-direct products, professionally installed by factory trained installers. Locally-owned. GAF Master Elite roofing certification.

"They're expensive and they did good work, but the details were not handled well: 1) They said the job would take one day - it took four. 2) They parked a large metal dumpster on my drive without prior warning, blocking my car in the garage making it impossible for me to leave. 3) They incorrectly calculated the final bill, only reducing it to the agreed upon amount after I pointed the mistake out. Also, this isn't a big deal but their sales reps, while friendly and knowledgeable, did the whole used-car sales "let me talk to the owner and try to get you a better deal," routine which was a bit corny and embarrassing. I understand that's what is still taught in sales rep school, but it feels a bit patronizing. When I said I needed a couple days to compare their offer with other estimates, they went into high pressure mode, using the old "I can't guarantee this price will last, etc. etc." all very old fashioned sales tactics that I hope companies will abandon soon. "

Michael W on October 2025

Since 1994, Air Tite Exteriors has provided homeowners in Maryland and D.C with top quality, factory-direct products, professionally installed by factory trained installers. Locally-owned. GAF Master Elite roofing certification.

"They're expensive and they did good work, but the details were not handled well: 1) They said the job would take one day - it took four. 2) They parked a large metal dumpster on my drive without prior warning, blocking my car in the garage making it impossible for me to leave. 3) They incorrectly calculated the final bill, only reducing it to the agreed upon amount after I pointed the mistake out. Also, this isn't a big deal but their sales reps, while friendly and knowledgeable, did the whole used-car sales "let me talk to the owner and try to get you a better deal," routine which was a bit corny and embarrassing. I understand that's what is still taught in sales rep school, but it feels a bit patronizing. When I said I needed a couple days to compare their offer with other estimates, they went into high pressure mode, using the old "I can't guarantee this price will last, etc. etc." all very old fashioned sales tactics that I hope companies will abandon soon. "

Michael W on October 2025

Avatar for Complete Exteriors, LLC

Complete Exteriors, LLC

6102 Cool Spring Terrace South
4.68(
64
)
•Approved Pro

Complete Exteriors, LLC

6102 Cool Spring Terrace South
4.68(
64
)
•Approved Pro
Customers say: True professional
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
53 local quotes requested

Here at Complete Exteriors we are driven by two things. Offering a complete and professional job completion, and doing what we say we will. We know what the frustrations are of the homeowner, When we tell you we will meet you at a time and date, we will be there! When we say we will complete the job on a certain date, we will! You shouldn’t hope to have a professional job done by a contractor - you should expect it!

"We had our roof replaced. Communication was very clear as to price, options and timing. The job was done on time and to full satisfaction. We would hire this firm again without hesitation."

Shawn K on September 2025

Here at Complete Exteriors we are driven by two things. Offering a complete and professional job completion, and doing what we say we will. We know what the frustrations are of the homeowner, When we tell you we will meet you at a time and date, we will be there! When we say we will complete the job on a certain date, we will! You shouldn’t hope to have a professional job done by a contractor - you should expect it!

"We had our roof replaced. Communication was very clear as to price, options and timing. The job was done on time and to full satisfaction. We would hire this firm again without hesitation."

Shawn K on September 2025

AML Top Quality Construction

105 Port Court
4.83(
21
)
•Approved Pro

AML Top Quality Construction

105 Port Court
4.83(
21
)
•Approved Pro
Customers say: Quick response
16 years of experience
Free onsite estimate

AML Top Quality Construction is a locally owned and operated company, serving the Grasonville, MD area and surrounding communities. We will help you create that indoor living space you have always dreamed of! From your kitchen, to your bathroom, or your basement, we can upgrade or give you that dream space. We offer professional craftsmanship, reasonable rates, and friendly customer service. Call us now!

"We are very pleased with the quality of work and the professionalism of Casey and the AML crew. The work was completed in the timeframe we requested and within the price range we expected. Casey was extremely responsive to emails and text messages and adaptable to change requests. The crew was very respectful and accommodating in their work schedule and did a great job keeping the construction area safe and clean. We were very pleased and plan to use them again for future projects."

Larry F on September 2025

AML Top Quality Construction is a locally owned and operated company, serving the Grasonville, MD area and surrounding communities. We will help you create that indoor living space you have always dreamed of! From your kitchen, to your bathroom, or your basement, we can upgrade or give you that dream space. We offer professional craftsmanship, reasonable rates, and friendly customer service. Call us now!

"We are very pleased with the quality of work and the professionalism of Casey and the AML crew. The work was completed in the timeframe we requested and within the price range we expected. Casey was extremely responsive to emails and text messages and adaptable to change requests. The crew was very respectful and accommodating in their work schedule and did a great job keeping the construction area safe and clean. We were very pleased and plan to use them again for future projects."

Larry F on September 2025

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
Super Service Award
Customers say: True professional
Recommended by 99% of Angi customers
Recommended by 99% of HomeAdvisor customers
189 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 Home Genius Exteriors

Home Genius Exteriors

8201 Corporate Dr.
4.87(
282
)
•Approved Pro

Home Genius Exteriors

8201 Corporate Dr.
4.87(
282
)
•Approved Pro
Super Service Award
Customers say: Super punctual
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
4511 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!

"Home Genius Came by to install a roof on my home! The project was completed in a timely fashion and the crew worked very hard and was professional throughout the process! And the job was done well and to my standards. The sales rep Ty Pearmon was very professional, knowledgeable and explained all of the products and process regarding my roof. And the project manager Angel Martinez was very attentive to my every question and concern, and even explained the process of the roof with photos and expertise. Thank you to home Genius for their hard work and professionalism. I would recommend them to all family and friends!"

Alfreda E on September 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!

"Home Genius Came by to install a roof on my home! The project was completed in a timely fashion and the crew worked very hard and was professional throughout the process! And the job was done well and to my standards. The sales rep Ty Pearmon was very professional, knowledgeable and explained all of the products and process regarding my roof. And the project manager Angel Martinez was very attentive to my every question and concern, and even explained the process of the roof with photos and expertise. Thank you to home Genius for their hard work and professionalism. I would recommend them to all family and friends!"

Alfreda E on September 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
396 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! admin@exquisiteroofing.com 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! admin@exquisiteroofing.com 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 Power Home Remodeling

Power Home Remodeling

12101 Tech Road
4.31(
838
)
•Approved Pro

Power Home Remodeling

12101 Tech Road
4.31(
838
)
•Approved Pro
Super Service Award
Customers say: Quality work
3044 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.

"Power Home Remodeling has been fantastic. We had them come out to replace our gutters and were very impressed with the quality of their work. The crew that did the job kept everything clean and organized; you wouldn’t have known they had been there, which is uncommon for many companies. We were so impressed that we are now moving forward with replacing our siding. Everyone at Power Home Remodeling has been incredibly helpful throughout this process, and we couldn’t be happier. We will work with them on future home projects."

Jonathan R on June 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.

"Power Home Remodeling has been fantastic. We had them come out to replace our gutters and were very impressed with the quality of their work. The crew that did the job kept everything clean and organized; you wouldn’t have known they had been there, which is uncommon for many companies. We were so impressed that we are now moving forward with replacing our siding. Everyone at Power Home Remodeling has been incredibly helpful throughout this process, and we couldn’t be happier. We will work with them on future home projects."

Jonathan R on June 2025

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
499 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

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FAQs for wood or fiber cement siding installation or complete replacement projects in Chestertown, MD

Yes, removing your existing siding before installing new cedar siding is essential for a secure and long-lasting installation. It helps eliminate hazards like rot and pest infestations and ensures a smooth surface for the new siding. Leaving old siding in place can compromise the appearance and integrity of your new cedar siding. Engaging a licensed siding contractor will ensure proper removal and preparation.

To determine how much cedar siding you'll need, start by measuring the height and width of each exterior wall of your home to calculate the area. For gable ends, measure from the base to the peak. Add up all these areas and then add an extra 10% to account for waste and future repairs. This ensures you purchase enough siding without running short.

Cedar siding endures between 20 and 40 years if maintained correctly from the start. This lifespan is secured by performing regular inspections for cracks, fungus, and bubbling and by pursuing consistent cleaning, painting, or staining with an appropriate sealant. Engaging a professional for periodic inspections ensures that your siding remains resilient and visually appealing for decades.

Your cedar siding must be maintained every three to five years through a thorough restaining or repainting process to preserve its strength and appearance. Regular maintenance prevents damage and ensures that the wood remains in peak condition. For homeowners seeking a less demanding upkeep schedule, choosing vinyl or aluminum siding offers a more resilient alternative while still providing exceptional style.

The Chestertown, MD homeowners’ guide to wood or fiber cement siding installations or complete replacements

From average costs to expert advice, get all the answers you need to get your job done.

See all articles
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