BOLDER. BETTER. TOGETHER.

We are thrilled to share some exciting news, Chesapeake Painting Services and Blue Star Paint & Property Services are joining forces. We are looking forward to bringing even more quality, expertise, and capability to our valued customers. Learn More

Home of the Gentlemen Contractors

This is what we do every day. We are highly skilled at interior painting, exterior painting, drywall repair, built-in shelving and closets, kitchens & baths, cabinet refinishing, and making your home beautiful.

We are an Annapolis, MD based painting company with over 25 years experience in residential and commercial painting. We constantly strive to provide the highest possible quality work and customer service available in the area at reasonable prices.

Top Rated Contractor in AA County

We take pride in transparency and our reviews! It is very easy for companies to TELL you about their quality work and to show you testimonials on their website, but we are happy to SHOW you our objective reviews on all of the top review sites because they are truly objective and our customers take time of their own to tell people about their experience with us.

Click any of the following below to read objective reviews by our customers.

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Call Us Today

(443)-569-2909

Residential & Commercial Services

High end quality interior painting services at affordable rates. This is what we built the business on with more than 25 years experience… Learn More

Nothing enhances the look and value of a home or building than a fresh exterior paint job and we have done hundreds of them… Learn More

Drywall installation is one of the most challenging jobs to do right. We have experts who focus exclusively drywall services… Learn More

Kitchen remodeling, flooring, countertops, painting & more. One of the best investments you can make in your home is in the kitchen… Learn More

Cabinet painting and refinishing can completely change the look of your kitchen and it’s less expensive than you think… Learn More

Our powerwashing crew will have your home, sidewalks, patios & entryways sparkle like they are brand new using top of the line equipment… Learn More

Our staining and sealing service will revitalize your decks and flooring, while protecting your driveways and surfaces for years to come… Learn More

Swap those IKEA shelves for the real thing and customize your closet to max its use with our custom closet and built-ins craftsmanship… Learn More

What Our Customers Are Saying…

Chesapeake Painting Services recently painted the entire exterior of our house, including power-washing, trim repair, and a few other issues discovered during the process. Scheduling was difficult because of the recent number of rain storms, but, knowing that we had a hard timeline to meet, the Chesapeake staff got the job done and the results are outstanding. As others have noted, communication is excellent and the staff is very responsive to questions. Cost was very, very competitive. Highly recommended.

Dawn S.

Annapolis

They did a range of services and they are really fantastic. Really good customer service.

Emily R.

There is no better painting company! I love the professionalism, care and attention everyone provides. They are trustworthy and top-notch painters. Having been a painter before (many moons ago), I know the degree of difficulty each project takes and the prep work that goes into it. They don't skimp on the prep, the painting, or the clean-up. Not only do they remake the look of a room with a simple change in color, but their drywall work is the best!!! I couldn't recommend Chesapeake Painting more.. You will be more than satisfied. And, I will continue to use them for my current house and future.

David Sonde

Odenton, MD

Our experience was amazing! The owner is so prompt with returning calls, answering questions and giving quotes. We owned a construction company for years and this company is top of the line! They arrived on time every day, the work they did was superb and we couldn't believe how clean they left the area they were working. We had them prime coat the area as well. We plan on spreading the word to friends and family. I also will call them in the future to do any paint/drywall projects that we may have in our home. Quality work is very hard to find these days and they far exceeded our expectations!

Barbara W.

Stevensville, MD

We have used this company for several jobs over the years. James and his crews are unfailingly prompt, professional, and clean, prices are reasonable especially given the consistent level of excellence, and I really can't say enough about how they care about the job before, during and even after. We've never had to clean up after them or worry about paint splatters or tracking on floors. Nor have we ever had to wait for them to show up for an estimate or a job. Truly a 5 star business.

Joanne Kagan

Annapolis, MD

Short and sweet here: Great job - Very detail oriented and spotless cleanup after each visit. Had kitchen cabinets painted and WOW, they look great! Will use again in the near future for painting projects. And very much enjoyed the customer service with everyone. Thank you!

John M

Hired to paint exterior trim, windows and window glaze. Very courteous and professional. Quality of work was decent for price paid. There were a few issues that needed follow-up, but they took care of them. Damaged gutters with ladder, but company stood behind it and replaced the section of gutter. More oversight by project manager/owner could have prevented most of the issues.

Chris S.

Annapolis, MD

Job went very extremely well. Chris was very helpful and organized the work around another company doing replacement of gutters. The painter assigned to our work was great. Painting was done carefully and area around house cleaned up well each night. We had squirrel damage near the roof line that required replacing some wood fascia and crown modeling. All the work was done well. We would strongly recommend this team to others.

Barbara Jacobs

Annapolis, MD.

Our experience with Chesapeake Painting was wonderful from the beginning. We liked what James said about the company so much - how they would respect our home, we didn't need to pay the balance until days later when we were totally satisfied, etc. - that we didn't even contact other painters. Gil and the crew that painted our living room, hall, and entry were professional and cared about the tiniest detail. We would highly recommend Chesapeake Painters.

BJ Robinson

Annapolis, MD

I was very impressed. James came out only a few hours after I had first called to give me an estimate. They were flexible when I needed to reschedule the work to start and advised me on how to deal with a difficult insurance company. Everything looks well-done and the team even repainted part of the bathroom for me. I would definitely recommend in the future.

Rachel Felver

Annapolis, MD

Great Job, start to finish. Excellent workers arrived on time and worked diligently all day on the prep work, first and second coats. They cleaned up each day and covered plants and brick work as they painted. It took only two full days to complete with the 5 person crew.

Nancy Snyder

Annapolis, MD

Chesapeake replaced a number of damaged cedar shake tiles and repainted a house on the property I manage. They arrived on schedule and completed the project within the timeline they provided. The workmanship is professional and the house looks fantastic. Even more impressive than the workmanship was the fact that Chesapeake proactively followed up with me to conduct a job completion walk-through. Many of the contractors I have worked with through the years try to avoid a walk-through when the job is finished.

Mark Schroeder

Baltimore, MD

Scheduling was easy, the workers arrived promptly at the appointed time and began work quickly thereafter. They managed to remove the wallpaper from two bathrooms and a powder room within the 8 hours of work that I purchased as a special offer. The guys were courteous, efficient, and professional.

Ralph Kwong

Crofton, MD

James and his crew did a great job repairing my drywall after I had plumbing replaced in my house. They were at my house at the scheduled time and completed the job in a professional and timely manner. The price they charged was very reasonable and didn't change even with a minor change to the work required. I would hire them again for any other drywall or painting work that I needed done.

Adam Werner

Odenton, MD

Excellent work. Completed earlier than estimated, professional crew, started early each morning and put in full days. Lowest of two estimates obtained by about $4,500, and final bill came in slightly below estimate. Would definitely recommend.

David Boyce

Arnold, MD

Wow! What an amazing, positive experience. We hired CPS to paint our kitchen, including the cabinets. From our first conversation with Lisa, through our consultation with Steve and Josh, and ending with their making sure we were completely satisfied, we could not be more delighted with their work. They are all professional perfectionists, and were meticulous in their preparation, painting and clean-up. Each and every employee was very personable, and took great pride in their work. I would highly recommend them for any painting project!

Sean L.

Annapolis, MD

Great communication. Really nice work for a reasonable cost.

Carolynn P.

Crofton, MD

I can't possibly convey enough of my gratitude for multiple jobs well done in my home by your painters. Your painters took such care with -- and pride in -- their work on both the interior and exterior. Thanks to their efforts with my kitchen cabinets, my kitchen looks absolutely brand new. The painters were a pleasure to have here in the house; both the preparation and clean-up were perfect. Their prices were excellent as well.

Carol L

I own a martial arts school (jiu-Jitsu) that is opening soon in maple lawn. I hired these guys to do the painting. The office manager, Lisa, was very responsive anytime I had a question or concern. They did an excellent job, and the owner, James, even came out to my location to make sure that everything met my expectations. They also gave me two pretty cool mugs as a gift. I would highly recommend their services to anyone looking for a good painting company that they can trust.

Scott N.

Laurel, MD

Thanks to the crew at Chesapeake Painting Services for getting our job quickly. We are putting our house on the market and needed to turn it around fast. After working with Chris they were on the job about a week after we got the estimate and finished on time. Angel who did the work was great and I would highly recommend them.

Mike Y

There is no better painting company! I love the professionalism, care and attention everyone provides. They are trustworthy and top-notch painters. Having been a painter before (many moons ago), I know the degree of difficulty each project takes. Not only do they remake the look of a room with a simple change in color, but their drywall work is bar none!!! I couldn't recommend Chesapeake Painting more.. You will be more than satisfied.

David S.

Washington, DC

Very impressed and pleased with the quality, speed, and cost of the service. In preparation for putting our house on the market, we needed most of the interior repainted. Chesapeake did an amazing job, and the process was so much easier and less expensive than we anticipated that we're kicking ourselves for not doing this years ago.

Melinda G.

I loved Chesapeake Painting Services! They did a phenomenal job removing my popcorn ceiling. It looks brand new. You would have never guessed there was gross, 80's popcorn ceiling there previously. The crew cleaned up before leaving every day. Then when they were completely done, they put everything back together how it originally was. Right down to the decor and throw pillows! I highly recommend them!

Natalie

Chesapeake painting did an outstanding job. The most challenging part of the job was prepping the stair woodwork. I wasn't fully satisfied with the initial work, and James sent his team back to correct the problem to my satisfaction. The quality of painting, the professionalism of the painters and their supervisors, and James' responsiveness were second to none. I plan to use Chesapeake Painting for future projects.

Charles Goldblum

Annapolis, MD

We had an excellent experience with Chesapeake Painting Services. They were very responsive to our needs and displayed professionalism from the office, to their customer service through to their workmanship. I will recommend them to everyone I know and will definitely use them for all my painting needs in the future.

Ellen C. Manassas

Annapolis, MD

Their estimate was significantly lower than some others I received, but James was very thorough in his estimate, so I had confidence that all the things I needed done were included. It was a big job, but they were careful to prep every area, caulk where needed, and then painted each area with the correct color (house has three colors). Job took 6 days, and the house looks fabulous. I also had them paint a couple rooms inside (walls and trim) and they did a wonderful job there as well. Would not hesitate to use them again (probably will soon).

Bobbi Collins

Annapolis, MD

Chesapeake Painting Services is OUTSTANDING!!! The owner, James Guth, and all of the employees are top notch. This time, they replaced rotted wood on the outside of the house and primed, caulked and painted it; replaced a vent; and secured the flashing above the windows and removed a rotten wood slat fence.

Mariana R.

Crofton, MD

I was very happy with the work Chesapeake Painting did at my house. James provided me with estimates on all the various work I needed done and completed it in a timely manner. James and Josh were both very considerate to my scheduling needs and made sure everything was perfect. I have used Chesapeake Painting for services in the past and will continue to call them in the future. I highly recommend them for quality work and professional, courteous service!

Corinne Smith

Annapolis, MD

Excellent work, would highly recommend. This is the 2nd time we've had them out to complete painting work and both times have been very pleased with the quality of the work and fair prices for a job well done. They were willing to work with a tight timeline we had and were professional at every step of the job.

Jaime W.

I needed some interior painting done and reached out to CPS for an estimate. James from CPS came out and he was very receptive and helpful to what I needed done. Based on our meeting, I thought James offered a competitive price and a lot of expert knowledge so I hired them on to paint most of the downstairs and the upstairs. It came out great! I highly recommend CPS and will use them in the future for any additional needs.

Phil B.

Annapolis, MD

Chesapeake painting did an amazing job on our home. We had painting, power washing, drywall repair and electrical work completed. The team that came to our home was friendly and professional. The management team stopped over several times to review work and provide feedback to the team. We are in the process of selling our home and James was able to squeeze in some additional work to get us on the market quickly! We will ALWAYS use Chesapeake Painting for our home improvement needs.

Rhonda Bittel

Annapolis, MD

I had Chesapeake Painting Services repaint the exterior trim and wooden surfaces on my house recently. The house is 50+ years old, and some areas required a lot of scraping and sanding to get a good surface. The crew took their time ensuring that everything was properly prepared before painting. Good finish, no drips, runs, overspray. Overall this was a great job. Reasonable price, professional crew, great results. And working with James to get an estimate and narrow down the scope of work was a pleasure. Thanks!

Patrick S.

Annapolis, MD

Why Choose Chesapeake Painting Services?

With so many painting contractors to choose from, why would you choose us? First, if you ever worked with us before, you know why, but for those who have not, allow us to explain.

The Gentlemen Painters

Most importantly, we are all gentlemen. Our team live up to a standard practically unknown to our industry.

Honesty

We are honest and will remain transparent throughout all phases of your project.

Quality

We insist on very high standards for quality and will not consider a job complete until the client is completely satisfied.

Pricing

We will not overcharge or coerce you into work that is not necessary or you do not want completed.

Cleanliness & Efficient

We are neat and will leave your place as we found it. We are efficient but will not rush.

Expertise

We have experts with decades of experience for each service we provide, especially our painting services.

Confidence

We sincerely believe we are the best painting contractor in Annapolis and the surrounding area.

Get Your Free Estimate Today!

We want to make sure you get what you are looking for at a price that keeps us in business and makes you happy. Our estimates are always free and we’ll surely provide a bit of advice whether we get the job or not.

We are thrilled to share some exciting news, Chesapeake Painting Services and Blue Star Paint & Property Services are joining forces. We are looking forward to bringing even more quality, expertise, and capability to our valued customers. Learn More

Home of the Gentlemen Contractors

Top Rated Contractor in AA County

Call Us Today

(443)-569-2909

Sign Up for Special Deals

Residential & Commercial Services

What Our Customers Are Saying…

Why Choose Chesapeake Painting Services?

With so many painting contractors to choose from, why would you choose us? First, if you ever worked with us before, you know why, but for those who have not, allow us to explain.

The Gentlemen Painters

Honesty

Quality

Pricing

Cleanliness & Efficient

Expertise

Confidence

Get Your Free Estimate Today!

We want to make sure you get what you are looking for at a price that keeps us in business and makes you happy. Our estimates are always free and we’ll surely provide a bit of advice whether we get the job or not.