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Top-Rated Painters in Upper Marlboro - Updated Nov 2026

Avatar for Annapolis Painting Services
Annapolis Painting Services
4.6(
125
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+10 more

Serving Upper Marlboro, 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%
3 neighbors recently requested a quote
Avatar for J.H Painting Services
J.H Painting Services
5.0(
25
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Upper Marlboro, 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."
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+82

Response time3 hrs
Response rate100%
Recommended by33%of homeowners
Avatar for Wilbers Painting
Wilbers Painting
4.8(
404
)
Painting or Staining - Small ProjectsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+13 more

Serving Upper Marlboro, MD and surrounding areas

Approved

In business since 2016

Free estimates

Emergency services offered

"Wilber's Painting was able to rehab the townhouse in an adequate amount of time. He knew that special paint needed to be applied to block odors and stains, before new paint could be applied to the walls and ceiling. He fixed ceilings with water damage and repaired drywall. He worked diligently and the rehab was very successful. I highly recommend Wilber's Painting."
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+166

Response time2 days
11 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Miguel Team LLC.
Miguel Team LLC.
4.9(
31
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+6 more

Serving Upper Marlboro, MD and surrounding areas

Approved

Emergency services offered

Customers say: True professional

"I had a great experience with Miguel Team LLC. for my deck staining project. The team was professional, punctual, and very detail-oriented. They took the time to properly prepare the deck and ensured the stain was applied evenly, which made a huge difference in the final result. My deck now looks refreshed and beautifully finished. They also kept the work area clean and communicated clearly throughout the process. I truly appreciate the quality of their work and would highly recommend them to anyone looking for reliable and high-quality deck staining services."
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+115

Response time2 days
Response rate97%
Recommended by62%of homeowners
Avatar for JK Paint by Design
JK Paint by Design
4.9(
20
)
Interior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + RoomsInterior Surfaces - Paint or Stain- For Business

Serving Upper Marlboro, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2017

Free estimates

Warranties offered

"Very courteous and professional. Did a wonderful job. Make sure you impress exactly what type of paint you want. We wound up with satin and we wanted semi-gloss. Also, make sure you remove all of your painting fixtures and electronic mounts ahead of time. They will be thrown away."
Blast of Learning Center
Blast of Learning Center
Blast of Learning Center
Blast of Learning Center
Blast of Learning Center

+11

Response time3 hrs
Response rate91%
37 neighbors recently requested a quote
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Showing 1-10 of 1421

FAQs for painting projects in Upper Marlboro, 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 Upper Marlboro, MD homeowners’ guide to painting services

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