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Top-Rated Painters in Oconomowoc - Updated Nov 2026

Avatar for DaVinci Painting
DaVinci Painting
5.0(
139
)
Interior Home or Surfaces - Paint or StainInterior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms+1 more

Serving Oconomowoc, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2004

Free estimates

Small jobs welcome

"I am so impressed by the work of Joel at DaVinci Painting! First of all, he is exactly on time every day and his attention to detail is top notch. He repaired a wall after a cabinet removal with no patch visible after painting. He works so diligently and independently that you can almost forget he is even there. Also, he uses paint that has a very low odor so you can actually sleep in a room the same day. Very happy with his work and will definitely be using him again for some more interior painting projects!"
Living room accent wall!
Living room.  Fireplace and surround.
Master bedroom window boxes and fireplace.
Entryway crown and pillars.
Living room walls and ceiling.

+9

Recommended by97%of homeowners
Avatar for 1451 Dale Painting
1451 Dale Painting
4.8(
39
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Oconomowoc, WI and surrounding areas

Approved

Super Service Award Winner

In business since 1994

Free estimates

Customers say: True professional

"Dale Painting was OUTSTANDING! I'd hire them again in a millisecond. They prepared a highly detailed bid that addressed all of my issues and put me at ease. Their price was lower than 5 of 6 companies I had bid on the job. They expertly helped me pick out the final colors that made feel comfortable going forward. They emptied all kitchen cabinets and removed many wall hangings and put them back exactly where they came from! And last but not least the finished painting job of all walls and ceilings looked superb. Excellent paint coverage, perfectly straight lines when abutting the ceiling or cabinets...no overspill. No paint drops or microsplaters anywhere. They totally covered all furnishings in plastic and taped ground cloth paper that couldn't move to the floor...very impressive. And to top it off they left me the unused paint in each of the five colors in case I need to do touch-ups down the road. 110% satisfaction with every single aspect of the job."
Recommended by77%of homeowners
Envision Professional Painting and Staining, LLC
5.0(
56
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+8 more

Serving Oconomowoc, WI and surrounding areas

Approved

In business since 2010

Free estimates

Customers say: Quick response

"Ramon and his crew did a fantastic job staining my deck and whitewashing the interior of my gazebo. In addition he pointed out other areas of the exterior of my home that needed attention which he also took care of. I plan on having Ramon come back to do some interior painting this fall after he completes his exterior jobs."
Response time5 hrs
Recommended by100%of homeowners
Avatar for Five Star Painting of Waukesha
Five Star Painting of Waukesha
4.8(
151
)
Interior Painting or Staining: 3 - 4 RoomsExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+3 more

Serving Oconomowoc, WI and surrounding areas

Approved

In business since 2016

Free estimates

Warranties offered

"Everything about our experience with Five Star Painting was top notch. We were contacted right away after having been referred to them. A project manager was scheduled to visit our home understand and quote our project in a very timely manner. The proposal was received quickly, and the project manager called me to discuss and clarify all details. The scheduling process was prompt and clear. The painters arrived on time and did an absolutely 100% FIVE STAR job. We will use Five Star Painting for all our future needs, and although it may clog up their schedule, we highly recommend Five Star Painting to everyone. We could not be more pleased with the results, and are enjoying our refreshed, updated spaces like never before!"
Before and After
Before and After
Before and After
Before and After
Before and After

+576

8 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Valencia Painting & More LLC
Valencia Painting & More LLC
5.0(
17
)
Exterior Home or Structure - Paint or Stain: MediumInterior Painting or Staining: 1 - 2 RoomsExterior Building - Paint or Stain - For Business+4 more

Serving Oconomowoc, WI and surrounding areas

Approved

In business since 2014

Free estimates

Warranties offered

"Hiring Mr Valencia was my best hire this year. My 2 bathrooms needed extra work done before the painting began and afterwards and he did it before making sure that everything was cleaned up. I will 100 percent hire him for my interior staining and painting next year Lord willing"
Courtney
Courtney
Courtney
Courtney
Courtney

+35

Response time1 day
Response rate100%
2 neighbors recently requested a quote
...
Showing 1-10 of 362

FAQs for painting projects in Oconomowoc, WI

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 Oconomowoc, WI homeowners’ guide to painting services

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