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Find Painters in Shady Side

Avatar for Spiros Painting
Spiros Painting
4.7(
71
)
Interior Painting or Staining: 1 - 2 RoomsExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+18 more

Serving Shady Side, MD and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"The price was very reasonable and their attention to detail was incredible. They finished in under 2 days and even came back a third day when I wasn’t happy with the color in the basement (I originally asked them to simply touch up, but the paint didn’t match)."
Exterior Painting
Exterior Painting
Interior Painting
1 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Annapolis Painting Services
Annapolis Painting Services
4.6(
125
)
Interior Painting or Staining: 1 - 2 RoomsInterior Home or Surfaces - Paint or StainInterior Painting or Staining: 3 - 4 Rooms+10 more

Serving Shady Side, 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
Response rate100%
1 neighbors recently requested a quote
Avatar for J.H Painting Services
J.H Painting Services
5.0(
14
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Shady Side, MD and surrounding areas

Approved

In business since 2022

Free estimates

Customers say: True professional

"J.H. Painting Services did great exterior work on my home this weekend. I had exterior siding and deck power washed, front door painted, and brick foundation painted. All work was done at a high level of quality and in a timely manner. Communication for planning each of the tasks easy and reliable. Contractor arrived on time. I highly recommend for power washing and paint jobs."
Additional Photos
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+82

Response time3 hrs
Response rate100%
1 neighbors recently requested a quote
Avatar for Chesapeake Painting Services
Chesapeake Painting Services
4.8(
126
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+14 more

Serving Shady Side, MD and surrounding areas

Approved

In business since 2009

Free estimates

Warranties offered

"This was the first time we have used Chesapeake Painting Services for a painting project. They were simply outstanding. Easy scheduling, superior professionalism, high quality work, extremely professional and polite work crew. We will use this company again for any future painting services. Highly recommend!"
Interior Painting
Additional Photos
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+112

Response time1 day
1 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Dependable Painting Service LLC
Dependable Painting Service LLC
4.8(
32
)
Exterior Home or Structure - Paint or Stain: SmallMetal Roofing - PaintExterior Building - Paint or Stain - For Business+9 more

Serving Shady Side, MD and surrounding areas

Approved

In business since 2016

Free estimates

Credit card accepted

With several years experience, Dependable Painting Services,LLC works hard to bring each customer the best possible service and quality available. We look forward to working with you on your next project. We welcome your questions and thank you for your interest.

window coating preparation
front area painted blue
Exterior project
rear area painted blue
siding area painted in blue

+9

2 neighbors recently requested a quote
Recommended by100%of homeowners
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Showing 1-10 of 665

FAQs for painting projects in Shady Side, 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 Shady Side, MD homeowners’ guide to painting services

From average costs to expert advice, get all the answers you need to get your job done.