Top-rated painters.

Get matched with top painters in Upperville, VA

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Painters in Upperville

Avatar for Gibbs Painting
Gibbs Painting
4.8(
56
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Home or Structure - Paint or Stain: Small+7 more

Serving Upperville, VA and surrounding areas

Approved

In business since 1992

Free estimates

Emergency services offered

"I hired Gibbs Painting to make some drywall repairs following a kitchen remodel and had them paint the ceiling in two different rooms. My interaction with them was very professional. From the estimate to the completion of the work, everything went very well. They completed the work In the amount of time they stated, left the house in excellent condition, and the on-site team was very easy to work with. I would hire them again to do work inside my house and would recommend them to others."
Response time6 hrs
Response rate100%
Recommended by77%of homeowners
Avatar for Paint The DMV, LLC
Paint The DMV, LLC
4.9(
86
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsExterior Home or Structure - Paint or Stain: Large+3 more

Serving Upperville, VA and surrounding areas

Approved

Super Service Award Winner

In business since 2019

Free estimates

Credit card accepted

"Stephen and Marvin and their crew did an exceptional job from start to finish on our painting project. They are true painting professionals, and not only did they do a quality painting job but the whole experience of clean up and the time it took them to complete the project went very smoothly and at a very reasonable price! Without question we highly recommend Paint the DMV and would definitely use them again….they are the best!"
Exterior Deck Staining
Front before. Needs cleaning, but some marks are from constant sun.
Before
Old deck that needed new stain. Started replacing bad boards
Final product

+29

Response time12 hrs
2 neighbors recently requested a quote
Recommended by82%of homeowners
Kris' Painting Service Inc
4.4(
39
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+16 more

Serving Upperville, VA and surrounding areas

Approved

In business since 1999

Free estimates

Warranties offered

"They were excellent in both being timely and on the quality of their service. They took care of a little problem that they brought to our attention before we even noticed it. I would highly recommend Kris' Painting."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+43

Response time1 day
2 neighbors recently requested a quote
Recommended by83%of homeowners
Jeff Newlin Painting
4.8(
30
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+3 more

Serving Upperville, VA and surrounding areas

Approved

In business since 1982

Free estimates

Customers say: Quick response

"Jeff and his crew made my house look brand new, everything was done to my satisfaction with a couple of spots having to be gone over because of carpet installation. He returned the day after they finished and touched up. His crew patched places that I didn’t even realize needed to be patched. He painted everything, including closets and shelves. Wonderful work!"
Exteriors
Exteriors
Exteriors
Exteriors
Exteriors

+27

Response time2 hrs
Recommended by95%of homeowners
...
Showing 1-10 of 544

FAQs for painting projects in Upperville, VA

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 Upperville, VA homeowners’ guide to painting services

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