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Find Painters in Chestertown

Avatar for Annapolis Painting Services
Annapolis Painting Services
4.6(
125
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1980

Free estimates

Emergency services offered

"Cleaning went well with 3 guys and done in one day. They called to coordinate the day to start of the staining which let us avoid a dinner party we were having. A team of 8 stained for 2 consecutive days. They left the site clean. The price was about the same as we paid a one-man company 3 years earlier and about $1k less than another quote we got for the work. We were very pleased and will have them quote any future painting we need done."
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+28

Response time1 day
1 neighbors recently requested a quote
Recommended by91%of homeowners
Avatar for G&H Contractor Services, LLC
G&H Contractor Services, LLC
4.9(
14
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"Did not clean up items . left bag of garbage. Left a bag of spikes from the floor. Poked myself when I picked up the garbage. Removed the carpeting fine. Left the spikes around the edge of room."
new cabinetes
paint
floor install
repair b-window
roof

+8

Response time2 days
Response rate86%
Recommended by63%of homeowners
Avatar for 143 Painting
143 Painting
5.0(
1
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2000

Credit card accepted

Offers commercial services

143 Painting is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty and responsibility in all of our jobs. We are a locally owned and operated business with more than 20 years of experience serving Bernville and surrounding areas. There is no job too big, or too small for our team. Call today and let us put our experience to work for you!

Guest bedroom
Guest Bedroom
Master Bedroom
Corners
Small Guest Bedroom

+3

Recommended by100%of homeowners
Avatar for ShorePro Construction, LLC
ShorePro Construction, LLC
4.3(
27
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2016

Free estimates

Small jobs welcome

"The tile looked great! They were easy to work with & completed the work in a timely manner. I had to spend some time after they left cleaning up & scrubbing something off the vanity, toilet, & bathtub. I m not sure if it was from the grout or caulk. They were the only company I contacted that did everything they said they would do. I would definitely hire them again."
Response time10 hrs
Response rate86%
11 neighbors recently requested a quote
Avatar for CDC Panting
CDC Panting
5.0(
2
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2002

Free estimates

Offers commercial services

"Review for Caesar (Ceasar?) Caesar has done an amazing job helping me prepare the sale of my home. He has done all of the work inside to make my home a luxury experience. His dedication has been pivotal to helping me get my house on the market. He has been my painter and repair person for years, and he already helped me sell one of my homes in PA by upgrading and repairing the entire home. If you want someone who shows up and is committed to finishing the work with great quality, hire Caesar."
Family room Painting job
apartment rental office
Beauty salon
Beauty salon
School multi-purpose room

+3

1 neighbors recently requested a quote
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Showing 1-10 of 370

FAQs for painting projects in Chestertown, MD

Most homeowners opt for semi-gloss or high-gloss paint to make the baseboards stand out against the walls. If you’d rather keep things subtle, matching the wall sheen with eggshell or satin also works well. When your trim has nicks or dents, reach for a flatter, matte finish—it hides minor imperfections better than a shiny coat.

Stripping old paint from trim costs $1 to $3 per linear foot. Pros use specialized tools and techniques to lift away existing layers without gouging the wood, then prep the surface for a fresh finish. While it adds to your budget, proper removal protects the molding and sets the stage for a smoother, longer-lasting paint job.

Tackling the baseboards first often leads to crisper lines. Painting trim first lets you tape off the boards instead of the walls, so you’re less likely to splatter color where you don’t want it. Any stray marks on the wall get covered when you roll on the final coat, making the whole process faster and tidier.

You can absolutely paint baseboards in place. Leaving them installed avoids the risk of cracking or misaligning the boards when they’re reattached. With thorough cleaning, light sanding, and careful taping, a pro—or an experienced DIYer—can achieve a sharp, factory-smooth finish while saving you the hassle of prying off and reinstalling trim.

Painting almost always beats replacement in cost. Swapping out baseboards runs about $150 in DIY materials or roughly $1,100 with a pro, while repainting costs about $50 in supplies and $1 to $5 per square foot for labor. Unless the boards are warped or severely damaged, a fresh coat delivers the same visual upgrade for a fraction of the price.

Paintable caulk and wood filler are the go-to fixes for nail holes in baseboards. Wood filler sands flush for a glass-smooth surface, while caulk provides a flexible seal that won’t crack as the house settles. Either way, patching those tiny divots before you prime ensures your finished baseboards look seamless.

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.