
Get matched with top painters in Chestertown, MD
There are 8 highly-rated local painters.
Need a pro for your painting project in Chestertown, MD?
TRUSTED BY CHESTERTOWN, MD HOMEOWNERS
4.8
Average homeowner rating74
Verified painting services reviews
Verified Reviews for Painting pros in Chestertown, MD
*The Angi rating for 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 Painting needs.
*The HomeAdvisor rating for 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 Painting needs.
Last update on December 01, 2025
Find Painters in Chestertown

Home Genius Exteriors
Home Genius Exteriors
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!
"Tony was my project manager him and his crew did a phenomenal job "
Herndon L on November 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!
"Tony was my project manager him and his crew did a phenomenal job "
Herndon L on November 2025

Home Genius Exteriors
Home Genius Exteriors
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!
"I would give this company a very high rating. They were extremely professional, cleaned up amazing, and we experienced no issues whatsoever. I would recommend them to anybody looking for home repairs, as they are an excellent company."
Melvin L on November 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!
"I would give this company a very high rating. They were extremely professional, cleaned up amazing, and we experienced no issues whatsoever. I would recommend them to anybody looking for home repairs, as they are an excellent company."
Melvin L on November 2025

AROCON Roofing & Construction
AROCON Roofing & Construction
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

Annapolis Painting Services
Annapolis Painting Services
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

Stiles Professional Painting, LLC
Stiles Professional Painting, LLC
We're a locally owned and operated company with over 38 years of industry experience. We value honesty and integrity and treat your property as if it were our own. Our company specializes in custom paint finishes, but we pride ourselves on the quality of our work as well as our commitment to outstanding results regardless of the job. We offer a variety of home improvement services that are customizable to each individual project. We look forward to building lasting relationships with our clients and guarantee your satisfaction!
"Mr. Stiles and his helper did quality work. They started and schedule and finished on time. His estimate was competitive with other bids. They were neat in their work and cleaning up after themselves. We needed a small amount of carpentry/repair; they did a good job with it. It was a pleasure doing business with Mr. Stiles."
James S on July 2020
We're a locally owned and operated company with over 38 years of industry experience. We value honesty and integrity and treat your property as if it were our own. Our company specializes in custom paint finishes, but we pride ourselves on the quality of our work as well as our commitment to outstanding results regardless of the job. We offer a variety of home improvement services that are customizable to each individual project. We look forward to building lasting relationships with our clients and guarantee your satisfaction!
"Mr. Stiles and his helper did quality work. They started and schedule and finished on time. His estimate was competitive with other bids. They were neat in their work and cleaning up after themselves. We needed a small amount of carpentry/repair; they did a good job with it. It was a pleasure doing business with Mr. Stiles."
James S on July 2020

Remodeling Wizards of Maryland
Remodeling Wizards of Maryland
Remodeling Wizards of Maryland is your one stop shop for ALL your Remodeling needs! Remodeling Wizards of Maryland is a family owned and operated company where our customers are treated like family. We strive to offer superior products at reasonable cost . We pride ourselves on insuring customer satisfaction and always look forward to a returning customer or a referral. Simply put, we bend over backwards, jump through any hoops, and cross any bridge to make sure that our customers are 110% satisfied.Cost of project is by job with care given to each and every customer and project. Owners John Capozzi and Marirose Capozzi. 443-310-2484
"I am very pleased with Remodeling Wizards of Maryland. I was super happy with the deck work that has been completed. I have used this company for many different projects over 2 homes and about 10 years. Thanks!"
Matthew U on October 2020
Remodeling Wizards of Maryland is your one stop shop for ALL your Remodeling needs! Remodeling Wizards of Maryland is a family owned and operated company where our customers are treated like family. We strive to offer superior products at reasonable cost . We pride ourselves on insuring customer satisfaction and always look forward to a returning customer or a referral. Simply put, we bend over backwards, jump through any hoops, and cross any bridge to make sure that our customers are 110% satisfied.Cost of project is by job with care given to each and every customer and project. Owners John Capozzi and Marirose Capozzi. 443-310-2484
"I am very pleased with Remodeling Wizards of Maryland. I was super happy with the deck work that has been completed. I have used this company for many different projects over 2 homes and about 10 years. Thanks!"
Matthew U on October 2020

Sparkling Image Roof & Exterior Cleaning
Sparkling Image Roof & Exterior Cleaning
Have you been looking for a trustworthy, reliable roof cleaner or pressure washing company to take care of your roof or exterior cleaning needs? Well look no further, the search is over!!! "Sparkling Image Roof & Exterior Cleaning" is the premier roof cleaning and pressure washing company serving Delaware, Maryland and Pennsylvania, specializing in roof cleaning and pressure washing. We are family owned, licensed and Insured company built on a foundation of personal service, quality work, professional results and great rates, but more importantly customer satisfaction. Family owned.
"Shawn Tiller did an excellent job. He showed up for all appointments on time, completed the job as promised and was very courteous. I would highly recommend his company."
Phyllis R on July 2018
Have you been looking for a trustworthy, reliable roof cleaner or pressure washing company to take care of your roof or exterior cleaning needs? Well look no further, the search is over!!! "Sparkling Image Roof & Exterior Cleaning" is the premier roof cleaning and pressure washing company serving Delaware, Maryland and Pennsylvania, specializing in roof cleaning and pressure washing. We are family owned, licensed and Insured company built on a foundation of personal service, quality work, professional results and great rates, but more importantly customer satisfaction. Family owned.
"Shawn Tiller did an excellent job. He showed up for all appointments on time, completed the job as promised and was very courteous. I would highly recommend his company."
Phyllis R on July 2018
JC Services
JC Services
JC Services is a locally owned and operated, licensed and insured company, with over 15 years of experience in the roofing and siding industry. We are an Owens Corning Preferred Contractor, a member of the Better Business Bureau and an Angie's List Contractor. We take pride in our work and stand behind it 100%. Customer satisfaction is our top priority. JC Services keeps our customers informed through their entire project from start to finish. We use only the finest materials and are still able to offer great prices. Call or email us to speak to us about your project. Estimates are always free and there is no obligation. As always our estimates are from the company owner, not a salesman, so our estimates are NO pressure.
"I don’t usually write recommendations, but rarely do you come across an individual or company that takes this much pride in his workmanship and instills these same qualities into his employees, and it shows. Joe Call is a local contractor who was recommended to my wife and I and we are very happy with our roof and gutters that JC Services installed. Joe and his team were prompt, professional and extremely courteous throughout the entire job. They worked diligently and quickly while taking every precaution to ensure all the debris was disposed of properly. The job was meticulously maintained. The entire experience was positive and hassle free. If you are looking for a professional and experienced local roofer, gutter, and siding expert, JC Services is without a doubt the best choice for the job. [email protected]"
Bill M on September 2019
JC Services is a locally owned and operated, licensed and insured company, with over 15 years of experience in the roofing and siding industry. We are an Owens Corning Preferred Contractor, a member of the Better Business Bureau and an Angie's List Contractor. We take pride in our work and stand behind it 100%. Customer satisfaction is our top priority. JC Services keeps our customers informed through their entire project from start to finish. We use only the finest materials and are still able to offer great prices. Call or email us to speak to us about your project. Estimates are always free and there is no obligation. As always our estimates are from the company owner, not a salesman, so our estimates are NO pressure.
"I don’t usually write recommendations, but rarely do you come across an individual or company that takes this much pride in his workmanship and instills these same qualities into his employees, and it shows. Joe Call is a local contractor who was recommended to my wife and I and we are very happy with our roof and gutters that JC Services installed. Joe and his team were prompt, professional and extremely courteous throughout the entire job. They worked diligently and quickly while taking every precaution to ensure all the debris was disposed of properly. The job was meticulously maintained. The entire experience was positive and hassle free. If you are looking for a professional and experienced local roofer, gutter, and siding expert, JC Services is without a doubt the best choice for the job. [email protected]"
Bill M on September 2019

MPW Painting/Maryland Pro Wash
MPW Painting/Maryland Pro Wash
Maryland Pro wash is an independent locally owned small business. We have been in business for over 10 years. Maryland pro wash is one of the areas only contractor using the industries latest and most advanced soft wash technology. We also go by MPW Painting and MPW Basement remodeling. Our MHIC #103189.
"great service and price."
Ligong Z on May 2024
Maryland Pro wash is an independent locally owned small business. We have been in business for over 10 years. Maryland pro wash is one of the areas only contractor using the industries latest and most advanced soft wash technology. We also go by MPW Painting and MPW Basement remodeling. Our MHIC #103189.
"great service and price."
Ligong Z on May 2024

The House Surgeon
The House Surgeon
The House Surgeon Home Improvement Company, LLC is Locally Owned & Family Operated. We provide Industry standard agreements detailing all transactions, proposed work and warranty information. Our Craftsman are Clean, Safe, Service Professionals wearing clearly identifiable uniforms. We charge by the job never by the hours and there's never an after hours fee.
The House Surgeon Home Improvement Company, LLC is Locally Owned & Family Operated. We provide Industry standard agreements detailing all transactions, proposed work and warranty information. Our Craftsman are Clean, Safe, Service Professionals wearing clearly identifiable uniforms. We charge by the job never by the hours and there's never an after hours fee.
The Chestertown, MD homeowners’ guide to painting services
From average costs to expert advice, get all the answers you need to get your job done.

The cost to stain a deck varies depending on its size, location, and type of stain. Keep reading to learn more about how much you might spend.

The cost to sandblast your home’s exterior or another surface on your property depends on the method and the materials you use. Learn more with this guide.

The cost to paint a stucco house depends on its size, the type of paint used, and any required repairs. This guide will help you budget for the painting project.

Painting a brick house is a permanent renovation project that requires weighing the pros and cons. Keep reading to find out if you should paint your brick home.

What’s the difference between interior and exterior paint? Knowing how they vary is key to understanding why you should never substitute one for the other.

What is the best type of paint for exterior homes? Keep reading to narrow down your paint options once and for all.
- Worton, MD Painters
- Rock Hall, MD Painters
- Kennedyville, MD Painters
- Church Hill, MD Painters
- Centreville, MD Painters
- Sudlersville, MD Painters
- Millington, MD Painters
- Galena, MD Painters
- Queenstown, MD Painters
- Earleville, MD Painters
- Henderson, MD Painters
- Edgewood, MD Painters
- Queen Anne, MD Painters
- Perryman, MD Painters
- Essex, MD Painters
- Middle River, MD Painters
- Cecilton, MD Painters
- Grasonville, MD Painters
- Belcamp, MD Painters
- Riverside, MD Painters
- Chester, MD Painters
- Joppa, MD Painters
- Goldsboro, MD Painters
- White Marsh, MD Painters
- Abingdon, MD Painters
- Aberdeen, MD Painters
- Marydel, DE Painters
- Dundalk, MD Painters
- Ridgely, MD Painters
- Clayton, DE Painters
- Interior Painting in Chestertown
- Exterior Painting in Chestertown
- Fence Painting in Chestertown
- Deck Staining in Chestertown
- Wallpaper Removal in Chestertown
- Popcorn Ceilings in Chestertown
- Drywall in Chestertown
- Plaster Plaster Repair in Chestertown
- Caulking Services in Chestertown
- Pressure Washing in Chestertown
- Deck Maintenance in Chestertown
- Deck Repair in Chestertown
- Wrought Iron Fencing Repair in Chestertown
- Bathroom Fan Installation in Chestertown
- Stair Companies in Chestertown
- Epoxy Flooring in Chestertown
- Wall Repair in Chestertown
- Windows in Chestertown
- Mailbox Repair in Chestertown
- Install Stair Railings in Chestertown
- Stucco in Chestertown
- Doors in Chestertown
- Closets in Chestertown
- Wood Stripping Companies in Chestertown
- Window Shutters in Chestertown
- Decks And Porches in Chestertown
- Window Shutter Repair in Chestertown
- Cabinet Contractors in Chestertown
- Repair Carport in Chestertown
- Window Door Contractors in Chestertown
- 🌱 "Mow a small front yard"
- 🛠 "Fix a leaking pipe under the sink"
- 🏠 "Repair shingles on an asphalt roof"





