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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

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Find Deck and porch pros in Chestertown

"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


Avatar for Canales Service, LLC

Canales Service, LLC

4.88(
105
)
Approved Pro

Canales Service, LLC

4.88(
105
)
Approved Pro
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
2018 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


Avatar for Fence & Deck Connection Inc

Fence & Deck Connection Inc

4.80(
179
)
Approved Pro

Fence & Deck Connection Inc

4.80(
179
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
1991 years of experience

With two locations in Annapolis and Millersville, Fence & Deck Connection has been the most trusted fence and deck contractor serving Maryland since 1991. We specialize in designing and installing fences, decks, and screened porches that enhance your outdoor living space - all backed by a Lifetime Structural Warranty. With a focus on quality craftsmanship and exceptional customer service, we bring your backyard goals to life. Whether you're upgrading your backyard or securing your property, trust the experts at Fence & Deck Connection. We have since expanded into Delaware, Richmond, Virginia, and Savannah, Georgia.

"I was impressed by the results that the team that build our new deck (John K., Teo, Fernando, and Lester) produced. They accurately followed the agreed upon design, adapting professionally as necessary to any surprises they encountered, ultimately designing and building a deck that exceeded my expectations. It's beautiful and sturdy - and construction itself took only 2 days, from start to finish! Our family and neighbors have already complimented it without solicitation, and I won't hesitate to recommend Fence & Deck Connection to my friends, neighborhood, and family as a result of the efforts of the team that I named here!"

Evan G on June 2025

With two locations in Annapolis and Millersville, Fence & Deck Connection has been the most trusted fence and deck contractor serving Maryland since 1991. We specialize in designing and installing fences, decks, and screened porches that enhance your outdoor living space - all backed by a Lifetime Structural Warranty. With a focus on quality craftsmanship and exceptional customer service, we bring your backyard goals to life. Whether you're upgrading your backyard or securing your property, trust the experts at Fence & Deck Connection. We have since expanded into Delaware, Richmond, Virginia, and Savannah, Georgia.

"I was impressed by the results that the team that build our new deck (John K., Teo, Fernando, and Lester) produced. They accurately followed the agreed upon design, adapting professionally as necessary to any surprises they encountered, ultimately designing and building a deck that exceeded my expectations. It's beautiful and sturdy - and construction itself took only 2 days, from start to finish! Our family and neighbors have already complimented it without solicitation, and I won't hesitate to recommend Fence & Deck Connection to my friends, neighborhood, and family as a result of the efforts of the team that I named here!"

Evan G on June 2025


Avatar for AROCON Roofing & Construction

AROCON Roofing & Construction

4.51(
1,357
)
Approved Pro

AROCON Roofing & Construction

4.51(
1,357
)
Approved Pro
Customers say: Quality work
2008 years of experience
Free onsite estimate

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


Avatar for Annapolis Painting Services

Annapolis Painting Services

4.70(
120
)
Approved Pro

Annapolis Painting Services

4.70(
120
)
Approved Pro
Customers say: Super punctual
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
1980 years of experience

The #1 Painting Contractor in Annapolis, Baltimore and the District of Columbia. Over 30 years of top quality service! Annapolis Painting Services has over 75 skilled craftsmen so that we can meet the demands for the residents in the Annapolis, Baltimore and the Washington DC Metro regions. We feature the kind of professional and technical dexterity to go from one specific project to another that may be quite different, which simply indicates we have all of the seasoned experience and training you can want from a painting company. Our clients love us because we proficiently handle all painting requests, both internal and external, for a myriad of properties. No job is too large or small, and they include residential, commercial, industrial, institutional, real estate projects and more. It is all about making your property look its best, which is why we handle related tasks such as: Interior & Exterior painting, Drywall repair & installation Roofing repair & installation, Siding repair & installation, Pressure washing... Plus many more services. Choose the BEST.. Choose APS!

"David and Christian were very professional and helped us get our ceiling painted without issue! They said it would be a two day project and ended up being just complete in one! Thankful for their services and Annapolis Painting for the great service."

Melvin S on May 2023

The #1 Painting Contractor in Annapolis, Baltimore and the District of Columbia. Over 30 years of top quality service! Annapolis Painting Services has over 75 skilled craftsmen so that we can meet the demands for the residents in the Annapolis, Baltimore and the Washington DC Metro regions. We feature the kind of professional and technical dexterity to go from one specific project to another that may be quite different, which simply indicates we have all of the seasoned experience and training you can want from a painting company. Our clients love us because we proficiently handle all painting requests, both internal and external, for a myriad of properties. No job is too large or small, and they include residential, commercial, industrial, institutional, real estate projects and more. It is all about making your property look its best, which is why we handle related tasks such as: Interior & Exterior painting, Drywall repair & installation Roofing repair & installation, Siding repair & installation, Pressure washing... Plus many more services. Choose the BEST.. Choose APS!

"David and Christian were very professional and helped us get our ceiling painted without issue! They said it would be a two day project and ended up being just complete in one! Thankful for their services and Annapolis Painting for the great service."

Melvin S on May 2023


Avatar for Cornerstone Hydrowash

Cornerstone Hydrowash

4.86(
18
)
Approved Pro

Cornerstone Hydrowash

4.86(
18
)
Approved Pro
Customers say: Terrific value
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
2003 years of experience

Cornerstone Hydrowash is a locally owned and operated company that values honesty and integrity, and stands behind our work. We specialize in exterior power washing and deck cleaning & sealing. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building long-term relationships with our clients and guarantee your satisfaction!

"Brian and Joy are wonderful at Cornerstone! We have used them regularly on both of our homes. They are professional and provide excellent service both homes and decks are sparkling clean. Thank you so much Brian and Joy! Kind regards, Toni"

Dr T on June 2025

Cornerstone Hydrowash is a locally owned and operated company that values honesty and integrity, and stands behind our work. We specialize in exterior power washing and deck cleaning & sealing. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building long-term relationships with our clients and guarantee your satisfaction!

"Brian and Joy are wonderful at Cornerstone! We have used them regularly on both of our homes. They are professional and provide excellent service both homes and decks are sparkling clean. Thank you so much Brian and Joy! Kind regards, Toni"

Dr T on June 2025


Apex Remodeling

4.66(
217
)
Approved Pro

Apex Remodeling

4.66(
217
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
1993 years of experience

Apex Remodeling is dedicated to providing the finest in building & home improvements from Custom Turn Key Additions from Design to Completion, Major Interior & Exterior Renovations, Designer Remodels to Beautiful Custom Flooring, Custom Interior & Exterior Painting, Custom Designed Stone & Tile for gorgeous Bathrooms, Kitchens, Fireplace Surrounds, Entry Ways & Room Accents to all Exterior Home Improvements including Siding: Vinyl, Wood, & Stucco in the color & style to perfectly match your home & budget, Energy Efficient Replacement Windows & Doors, Custom Deck Systems designed for you & more! We have an experienced crew of contractors & master craftsmen detailing your home to perfection with personalized professional service from start to finish!

"Our fence looks incredible! They came swiftly to do the work, and we still get compliments about how great our fence looks. We liked working with Henry. The first issue arose when the fence exceeded the quote and contract that we signed. We weren’t told this until the very end of the work, which was not great to say the least by an additional 20%. We knew there was some flexibility in the price, but it would’ve been nice to say, by the way, we’ve exceeded the estimated price and expect the final price to be in this range. Lastly, we also had issues with our gate hinges and called them back 3x until it was finally fixed. It was difficult to get them to come back out even though we were under warranty, and we encountered issues with their customer service and communication. We would probably still use them again for another fence but would only communicate with Henry."

Alex D on May 2025

Apex Remodeling is dedicated to providing the finest in building & home improvements from Custom Turn Key Additions from Design to Completion, Major Interior & Exterior Renovations, Designer Remodels to Beautiful Custom Flooring, Custom Interior & Exterior Painting, Custom Designed Stone & Tile for gorgeous Bathrooms, Kitchens, Fireplace Surrounds, Entry Ways & Room Accents to all Exterior Home Improvements including Siding: Vinyl, Wood, & Stucco in the color & style to perfectly match your home & budget, Energy Efficient Replacement Windows & Doors, Custom Deck Systems designed for you & more! We have an experienced crew of contractors & master craftsmen detailing your home to perfection with personalized professional service from start to finish!

"Our fence looks incredible! They came swiftly to do the work, and we still get compliments about how great our fence looks. We liked working with Henry. The first issue arose when the fence exceeded the quote and contract that we signed. We weren’t told this until the very end of the work, which was not great to say the least by an additional 20%. We knew there was some flexibility in the price, but it would’ve been nice to say, by the way, we’ve exceeded the estimated price and expect the final price to be in this range. Lastly, we also had issues with our gate hinges and called them back 3x until it was finally fixed. It was difficult to get them to come back out even though we were under warranty, and we encountered issues with their customer service and communication. We would probably still use them again for another fence but would only communicate with Henry."

Alex D on May 2025


Avatar for GLR Home Improvement

GLR Home Improvement

4.95(
19
)
Approved Pro

GLR Home Improvement

4.95(
19
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
2010 years of experience

We have over 30 years experience! Our company is based on the belief that our customers' needs are of the utmost importance. Our entire team is committed to meeting those needs. As a result, a high percentage of our business is from repeat customers and referrals. We would welcome the opportunity to earn your trust and deliver you the best service in the industry.

"Gary's work is excellent and both jobs were completed fast. I am hiring him again for another project."

Lee W on October 2025

We have over 30 years experience! Our company is based on the belief that our customers' needs are of the utmost importance. Our entire team is committed to meeting those needs. As a result, a high percentage of our business is from repeat customers and referrals. We would welcome the opportunity to earn your trust and deliver you the best service in the industry.

"Gary's work is excellent and both jobs were completed fast. I am hiring him again for another project."

Lee W on October 2025


Avatar for Blessed -2- Be Roofing LLC

Blessed -2- Be Roofing LLC

4.79(
19
)
Approved Pro

Blessed -2- Be Roofing LLC

4.79(
19
)
Approved Pro
Customers say: Quality work
2018 years of experience
Free onsite estimate

Blessed-2-Be Roofing LLC is a trusted, full-service roofing contractor dedicated to protecting and enhancing homes and businesses in the DMV area. With over 15 years of experience, our certified and insured team provides top-quality craftsmanship and uses the industry's best materials to deliver durable, long-lasting roofing solutions. We specialize in a wide range of services, including residential and commercial roof installation, replacement, repairs, and maintenance. From identifying the source of a leak to guiding you through a full-scale replacement, we are committed to providing transparent communication, fair pricing, and a stress-free experience. We also specialize in window, siding, and deck installations. Our mission is to put customer satisfaction first, ensuring every project is completed safely, efficiently, and to the highest standards. We stand behind our work with comprehensive warranties, so you can have peace of mind knowing your property is covered by the experts.

"Very professional. Team arrived on time and finished within one day with amazing results "

amira m on December 2025

Blessed-2-Be Roofing LLC is a trusted, full-service roofing contractor dedicated to protecting and enhancing homes and businesses in the DMV area. With over 15 years of experience, our certified and insured team provides top-quality craftsmanship and uses the industry's best materials to deliver durable, long-lasting roofing solutions. We specialize in a wide range of services, including residential and commercial roof installation, replacement, repairs, and maintenance. From identifying the source of a leak to guiding you through a full-scale replacement, we are committed to providing transparent communication, fair pricing, and a stress-free experience. We also specialize in window, siding, and deck installations. Our mission is to put customer satisfaction first, ensuring every project is completed safely, efficiently, and to the highest standards. We stand behind our work with comprehensive warranties, so you can have peace of mind knowing your property is covered by the experts.

"Very professional. Team arrived on time and finished within one day with amazing results "

amira m on December 2025


Avatar for G&H Contractor Services, LLC

G&H Contractor Services, LLC

4.86(
11
)
Approved Pro

G&H Contractor Services, LLC

4.86(
11
)
Approved Pro
Customers say: Quick response
2015 years of experience
Free onsite estimate

We value honesty and integrity and will treat your home improvement project as if it were our own. We offer a wide range of roofing expertise and experience to meet the specific needs of our clients. We specialize in a variety of roofing, to include asphalt shingle, traditional tile, natural slate, flat, foam, or single-ply. We pride ourselves on the quality of our work and offer a 2 year warranty on our services.

"They did an excellent job, exceeding my expectations. They covered all my furniture. They're a clean and hardworking team."

fred j on September 2025

We value honesty and integrity and will treat your home improvement project as if it were our own. We offer a wide range of roofing expertise and experience to meet the specific needs of our clients. We specialize in a variety of roofing, to include asphalt shingle, traditional tile, natural slate, flat, foam, or single-ply. We pride ourselves on the quality of our work and offer a 2 year warranty on our services.

"They did an excellent job, exceeding my expectations. They covered all my furniture. They're a clean and hardworking team."

fred j on September 2025

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Decks and Porches questions, answered by experts

Costs depend on dock size, material type, damage severity, labor, and required permits.

There are deck restoration products and oil-based wood stains that can help bring back some of the color and shine to your faded Trex decking. However, if your boards are suffering from serious fading due to UV rays or chemical cleaning products, don’t expect miracles. Also, these products are only suitable for use on the older Trex boards, not the capped, second-generation Trex products. 

Even if your deck is properly constructed with a solid foundation, it doesn’t always mean it can handle the extra weight of a sunroom. Always call in a structural engineer to perform a deck inspection to evaluate the quality and structural integrity of the deck before building. You may need to reinforce the foundations and joists, and with decks in poor condition, it might be better to tear them down and start again. A pro can help you decide.

A wood deck needs an annual cleaning, plus refinishing every two to three years, which involves sanding the deck and applying stain or sealer. If you have a painted deck, you’ll need to repaint it every 10 years. You should also fix and repair loose or broken deck boards, nails, and screws. Cleaning your deck regularly and applying sealant protects the wood from the elements, water damage, rot, mildew, and fading from the sun.

Deck repairs cost around $800 to $3,500. However, your cost depends on the type and severity of the repair, as well as the type of decking material you have. Other factors, like location and labor costs, impact the price, too. Boards and railings are the priciest parts of a deck to repair, while loose stairs are less expensive to fix.

The Chestertown, MD homeowners’ guide to deck and porch services

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