Get matched with top exterior painters in Chestertown, MD
There are 10 highly-rated local exterior painters.
TRUSTED BY CHESTERTOWN, MD HOMEOWNERS
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25 Verified Reviews for Exterior Painting pros in Chestertown, MD
*The Angi rating for Exterior Painting companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Exterior Painting needs.
*The HomeAdvisor rating for Exterior Painting companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Exterior Painting needs.
Last update on July 04, 2025
Exterior painters in Chestertown
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
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.
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!
"Everybody ive talked to starting with the sales rep Wu, down to Dylan the project manager, and especially Leo's roofing crew has been absolutely amazing. Even the folks behind the scenes communicated everything effortlessly, and my roof is excellent. Cannot speak highly enough about this experience."
Stephen M on June 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!
"Everybody ive talked to starting with the sales rep Wu, down to Dylan the project manager, and especially Leo's roofing crew has been absolutely amazing. Even the folks behind the scenes communicated everything effortlessly, and my roof is excellent. Cannot speak highly enough about this experience."
Stephen M on June 2025
We like to be professional and get the job done in a timely and good manner. We guarantee that everything will be done correctly. We do siding, painting, windows and door installation, flooring, remodeling, and roofing
"Outstanding. What I love about Andre Pasqual is his attention to detail. He makes sure he leaves the job looking flawless, and he is all about making the customer happy!"
Angelica . on December 2024
We like to be professional and get the job done in a timely and good manner. We guarantee that everything will be done correctly. We do siding, painting, windows and door installation, flooring, remodeling, and roofing
"Outstanding. What I love about Andre Pasqual is his attention to detail. He makes sure he leaves the job looking flawless, and he is all about making the customer happy!"
Angelica . on December 2024
Transformed Spaces: Transforming your home into a space you love We are a remodeling company dedicated to create unique and personalized spaces that reflect your lifestyle. We offer a wide range of services, from complete renovations of homes to minor updates, always with the aim of providing a high service quality and attention to detail. Our services: Complete home renovations: Kitchen, bathroom, bedrooms, living room, etc. Additions and expansions: More space for your family or for your hobbies Minor renovations: Painting, installation new flooring, cabinets, etc. ¡
Transformed Spaces: Transforming your home into a space you love We are a remodeling company dedicated to create unique and personalized spaces that reflect your lifestyle. We offer a wide range of services, from complete renovations of homes to minor updates, always with the aim of providing a high service quality and attention to detail. Our services: Complete home renovations: Kitchen, bathroom, bedrooms, living room, etc. Additions and expansions: More space for your family or for your hobbies Minor renovations: Painting, installation new flooring, cabinets, etc. ¡
We have a complete team that includes whole house painting, whole house water purification systems, plumbing systems, and whole house remodeling and renovations.
We have a complete team that includes whole house painting, whole house water purification systems, plumbing systems, and whole house remodeling and renovations.
At Ace Handyman Services, we offer a unique approach to home repairs and improvements. Unlike traditional service providers, we operate as a time and materials company, offering you the flexibility of purchasing a block of time tailored to your specific needs. This innovative approach allows you to maximize the value of our skilled craftsmen, who bring over 20 years of experience to the table. Rest assured, our licensed, bonded, and insured professionals are dedicated to your satisfaction, and with the backing of the trusted Ace Hardware brand, we're your partner for quality and reliability. Plus, we're proud to stand behind our work with a solid 12-month labor and materials warranty, ensuring your peace of mind. Choose Ace Handyman Services for a smarter way to tackle your home projects.
At Ace Handyman Services, we offer a unique approach to home repairs and improvements. Unlike traditional service providers, we operate as a time and materials company, offering you the flexibility of purchasing a block of time tailored to your specific needs. This innovative approach allows you to maximize the value of our skilled craftsmen, who bring over 20 years of experience to the table. Rest assured, our licensed, bonded, and insured professionals are dedicated to your satisfaction, and with the backing of the trusted Ace Hardware brand, we're your partner for quality and reliability. Plus, we're proud to stand behind our work with a solid 12-month labor and materials warranty, ensuring your peace of mind. Choose Ace Handyman Services for a smarter way to tackle your home projects.
We Provide any, Concrete, Stamped Concrete,Fence,Deck, Roofing & Paint Service. We have over 15 Years of Experience we always aim for Quality work & to please our customers, our work won't disappoint.
We Provide any, Concrete, Stamped Concrete,Fence,Deck, Roofing & Paint Service. We have over 15 Years of Experience we always aim for Quality work & to please our customers, our work won't disappoint.
Home Remodeling Services, LLC. Owner operator. Gabriel Galeano Tel 240-398-0471 with more than 25 plus years of experience in home remodeling. The Services provide are the follows: Carpentry, framing, tile, painting ( interior-exterior ), kitchen remodeling, bathroom remodeling, basement, decks, wallpaper, etc.
"Overall, it went well. We still have more to do…."
Claudia S on December 2023
Home Remodeling Services, LLC. Owner operator. Gabriel Galeano Tel 240-398-0471 with more than 25 plus years of experience in home remodeling. The Services provide are the follows: Carpentry, framing, tile, painting ( interior-exterior ), kitchen remodeling, bathroom remodeling, basement, decks, wallpaper, etc.
"Overall, it went well. We still have more to do…."
Claudia S on December 2023
FAQs for exterior painting projects in Chestertown, MD
You should paint your home exterior every five to 10 years, on average. Climate and surroundings can affect how well paint holds up. Wood siding will likely need a fresh coat of paint every three to seven years. Paint on brick tends to last about eight to 17 years, on average.
Calculate the square footage of the area you want to paint. Divide the square footage by 350 (the average square footage a gallon of paint covers). Multiply the number of gallons you need by two, as you’ll likely be applying two coats of paint. For a more accurate estimate, subtract the square footage of the windows and doors from the initial square footage total. It’s a good idea to plan for an extra gallon of paint to make sure you have enough to finish the job.
To calculate the square footage of a home exterior, painters multiply the length of the wall by the height of the wall to be painted. Then they add the total square footage for all of the walls to be painted. To calculate the price, they multiply the total square footage by their cost per square foot to prep and paint. Additional costs may factor in such as repairs, additional trim, and walls higher than the first story.
The cost to paint the exterior of a house ranges from $1,900 to $4,500 or about $1.50 to $4 per square foot, depending on the size, height, and complexity of the home layout. Other cost factors include your location, the type of siding (e.g., wood, aluminum, brick, stucco, etc.), and the kind of paint (e.g. oil-based, latex, acrylic, etc.). Painting the trim a different color or painting intricately designed trim can also increase the cost.
You should apply at least two coats of paint when painting the exterior of your house. Two coats of paint provides better durability and more even coverage than just one coat.
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