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

Annapolis painting company
annapolis painting
annapolis painting

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.

Angies List Reviews
Yelp Reviews
Google Reviews
Facebook Approved Reviews

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Residential & Commercial Services

Interior Painting

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

Exterior Painting

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 Services

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

Kitchen & Bath Renovations

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

Cabinet Refinishing

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

Powerwashing

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

Staining & Sealing

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

Built Ins & Closets

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…

Painting Reviews

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.

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.