Angie's List Award Winner

The #1 Rated Painting and Home Services Contractor on Angies List and Google Reviews,Yelp and Home Advisor. We can’t make this stuff up.

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.

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 its 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

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…

We take pride in transparency and our reviews! Click any of the following below
to read objective reviews by our customers.

Angies List Reviews
Yelp Reviews
Google Reviews
Home Advisor Approved Reviews
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.

  • Give us a sense of the work you are hoping to get done here or we can discuss on the phone. Either way we look forward to talking to you.