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Avatar for Five Star Painting of Madison
Five Star Painting of Madison
4.9(
51
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Watertown, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2000

Free estimates

Warranties offered

"5 Star Painting did a fabulous job on everything from helping us select the perfect color to meticulously painting the entire house and deck. We are so happy with the outcome. The entire process went very smoothly and we recommend them to anyone looking for painting services."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+606

Recommended by98%of homeowners
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Avatar for Joas Painting, LLC
Joas Painting, LLC
4.7(
46
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 5 + RoomsInterior Painting or Staining: 3 - 4 Rooms+1 more

Serving Watertown, WI and surrounding areas

Approved

In business since 2001

Free estimates

Customers say: Terrific value

"We recently had Joas Painting paint a large part of our home and 2 of our entry doors. They did an awesome job! The guys were all very friendly and anything we asked of them they tended too. I would highly recommend them. The painting they did was excellent and we are picky!! 5 stars"
Response time2 days
Response rate95%
2 neighbors recently requested a quote
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Avatar for Michael's Painting
Michael's Painting
4.4(
62
)
Interior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+2 more

Serving Watertown, WI and surrounding areas

Approved

In business since 1981

Free estimates

Emergency services offered

"Power washed house first then a few days later came back and painted the house really did a nice job"
Exterior Painting
Exterior Painting
Before
After
Before

+39

Response time2 days
1 neighbors recently requested a quote
Recommended by81%of homeowners
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Avatar for Santiago Home Improvement, LLC
Santiago Home Improvement, LLC
5.0(
99
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumInterior Painting or Staining: 3 - 4 Rooms+7 more

Serving Watertown, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2019

Free estimates

Warranties offered

"Santiago Painting did a fantastic job staining our deck! We had some problems with color matching and they were patient and helpful. They always responded quickly to our communications and were very knowledgeable. I will always use them if I need work done and highly recommend them! If you are looking for high quality and efficiency, hire Santiago Painting!"
Complete rebuilt!
Before and after
Siding repairs ✅
👍
Handrail repair

+7

Response time12 hrs
Response rate92%
67 neighbors recently requested a quote
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Avatar for CertaPro Painters
CertaPro Painters
4.3(
75
)
Exterior Home or Structure - Paint or StainInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Watertown, WI and surrounding areas

Approved

In business since 1971

Free estimates

Credit card accepted

"Professional free home estimate. On time, well priced and three painters arriving on time, time value and beautiful work and clean up. Highly recommend."
Garage Painting
Interior Prep
Exterior
Exterior
Interior

+1

Recommended by94%of homeowners
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Avatar for Delkamps Quality Improvements, LLC
Delkamps Quality Improvements, LLC
4.9(
9
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+8 more

Serving Watertown, WI and surrounding areas

Approved

In business since 2021

Free estimates

Small jobs welcome

"Very professional from start to finish. Always on time & quality work. Painted entire interior of our home including all trim work, walls, ceilings & closets. We are extremely happy with the results!"
After
After
Before vinyl plank flooring
Before drywall repair
After

+8

Response time6 hrs
Response rate100%
Recommended by75%of homeowners
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Avatar for S&S Painting and Restoration, LLC
S&S Painting and Restoration, LLC
3.9(
37
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+8 more

Serving Watertown, WI and surrounding areas

Approved

In business since 2016

Free estimates

Warranties offered

"We had a great experience completely remodeling a kitchen, two bathrooms, flooring, exterior paint and a fireplace restoration (and more). It was amazing working with Bob and the team and we just hired them for another project. Highly recommend."
After Restoration
Before Restoration
Before Restoration
After Restoration
Before Restoration

+14

Response time1 day
Response rate93%
67 neighbors recently requested a quote
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Avatar for Roman Landscaping and Snow Removal
Roman Landscaping and Snow Removal
5.0(
7
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+1 more

Serving Watertown, WI and surrounding areas

Approved

In business since 2014

Free estimates

Emergency services offered

"He redid my patio. Good work!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+9

Response time1 day
1 neighbors recently requested a quote
Recommended by100%of homeowners
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Avatar for Berry Remodel, LLC
Berry Remodel, LLC
5.0(
7
)
Interior Painting or Staining: 1 - 2 Rooms

Serving Watertown, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2023

Free estimates

Credit card accepted

"Jackson replaced trim work in two of my rooms and hallway. He paid attention to the details and style leaving me with a refreshed and professional look."
Fitchburg Cedar Deck
Fitchburg Cedar Deck
Verona Basement
Verona Basement
Verona Basement

+6

Response time5 hrs
Response rate100%
3 neighbors recently requested a quote
Request Quote
D and S Drywall
4.7(
3
)
Interior Painting or Staining: 1 - 2 RoomsInterior Surfaces - Paint or Stain- For BusinessPainting or Staining - Small Projects - For Business

Serving Watertown, WI and surrounding areas

Approved

In business since 2021

Free estimates

Emergency services offered

"He got right to work and did all the mudding in 2 1/2 hrs. Came back a couple days later, after it had dried and did the finishing and painting. Never took a break. Was reasonably priced too."
Response time7 hrs
Response rate100%
Recommended by33%of homeowners
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Showing 1-10 of 223

FAQs for painting projects in Watertown, 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 Watertown, WI homeowners’ guide to painting services

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

See all articles