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TRUSTED BY OREGON, WI HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon759
    Verified painting services reviews

Top-Rated Painters in Oregon - Updated Nov 2026

Avatar for Five Star Painting of Madison
Five Star Painting of Madison
4.9(
51
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Oregon, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2000

Free estimates

Warranties offered

"Five Star Painting was highly efficient and helpful throughout the process. Their explanations of the process, information on the procedure and paint/ stain choice, flexible scheduling, commitment to follow agreed-upon schedules, were welcome. They delivered a fantastic product, this with minimal interference with our own life routine, and at a highly competitive cost. I would recommand them to anyone interested in outdoor or indoor painting services."
Additional Photos
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+606

1 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Diaz Painting
Diaz Painting
5.0(
23
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or StainInterior Painting or Staining: 1 - 2 Rooms+5 more

Serving Oregon, WI and surrounding areas

Approved

In business since 2010

Free estimates

Offers commercial services

"Carlos and his crew were on time, friendly, efficient and tidy, cleaning up every day when they were finished. They did a fabulous job painting the interior of our townhome. They also patched and repaired dings in the walls prior to painting, often pointing out areas I would not have noticed. The walls and ceilings are now beautiful, thanks to them. I highly recommend Diaz Painting."
Response time1 day
3 neighbors recently requested a quote
Recommended by86%of homeowners
Avatar for College Works Painting - Madison
College Works Painting - Madison
4.3(
404
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large

Serving Oregon, WI and surrounding areas

Approved (Corporate)

In business since 1993

Free estimates

Warranties offered

"We are very impressed and pleased with working with Drew and his crew from our first meeting to the last walk around with Drew. They listened to what we pictured in our minds then guided us through the process of selecting colors. Drew and his crew started by pressure washing our home. Then they came and rapidly and professionally prepped our home for painting. Next the came and painted our home with the three colors we picked for different areas of the exterior of our home. They are great young men who worked not stop, always cleaned up at the end of the day. The entire process took four days. We have Cedar siding, many wood framed windows and cement block lower all being painted with three different stain and paint colors. They were courteous and positive and seemed to enjoy the work they did so well. We are completely satisfied with their professionalism and beautiful job they did on our home. John Bigham. Mankato Mn"
Exterior Painting
Exterior Painting
Exterior Painting
Exterior Painting
Exterior Painting

+12

Recommended by84%of homeowners
Avatar for Southeast Homeworks
Southeast Homeworks
5.0(
10
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+1 more

Serving Oregon, WI and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"Louis was very friendly and inquisitive during his walkthrough and was very forthright in the estimate provided. On our appointed day, Colin was prompt, friendly, and very skilled in getting our paint jobs done. We are very satisfied with the results and would recommend Southeast Homeworks and use their services again."
Geometric Mural 1
Geometric Mural 2
Dining Area
Classic Kitchen
Kitchen & Dining

+42

Response time3 hrs
Response rate100%
1 neighbors recently requested a quote
Avatar for 4 Lakes Painting, LLC
4 Lakes Painting, LLC
4.9(
9
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Oregon, WI and surrounding areas

Approved

In business since 2019

Free estimates

Credit card accepted

"Aneil and the staff were very professional. The project was thoroughly discussed with us before they started. Aneill made excellent color suggestions. They arrived when expected and completed the project when anticipated. The things in our home were well cared for while the crew was painting. I would recommend Aneil and 4 Lakes Painting to anyone!"
Historical Restoration
Historical Restoration
Response time3 days
Recommended by100%of homeowners
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 Oregon, WI and surrounding areas

Approved

In business since 1971

Free estimates

Credit card accepted

"The entire Certa Pro team supervised by Mario Mesa, was very polite, professional, extremely cooperative and very meticulous when it came to painting our home. We could not have asked for a better crew. They did an outstanding job. We would also like to thank Matt Unger our sales representative."
Garage Painting
Interior Prep
Exterior
Exterior
Interior

+1

Recommended by94%of homeowners
Avatar for O.G. Property Services
O.G. Property Services
4.9(
42
)
Painting or Staining - Small ProjectsPainting or Staining - Small Projects - For Business

Serving Oregon, WI and surrounding areas

Approved

Super Service Award Winner

Warranties offered

Customers say: True professional

"I don’t think there is anything Oscar can’t do. He put up screens, fixed electrical issues, installed an air conditioner, fixed door jams so that our doors would lock, added a handrail to the basement and sanded and painted holes on the wall. I can’t say enough good things about Oscar’s work. He is very personable too. I highly recommend Oscar for any job you might need done."
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+15

Response time3 days
Recommended by85%of homeowners
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Painting FAQs, answered by experts

While power washing isn't a requirement before you stain a fence, it can make the job much easier and faster while reducing manual labor requirements. The stain will not work if the wood is full of dirt and dust, so power washing, sometimes called pressure washing, is a fast and effective way to prepare the wood for staining. Remember that you need to stain or repaint relatively soon after the wood has dried so that there isn’t time for dust and dirt to build up again. 

Whether to brush or roll stain on wood depends on the project and your preference. Brushing is ideal for smaller, intricate areas and offers more control over the application, ensuring thorough coverage and penetration into the wood's grain. 

Conversely, rolling is efficient for more extensive, flat surfaces and can save time. However, it is not always the best fit for textured or uneven wood. Some projects may benefit from combining both methods, using a brush for detail work and a roller for broader areas. Ultimately, the choice between brushing and rolling depends on the specific requirements of your staining project.

You can use latex or acrylic paint outdoors. Although acrylic paint tends to last longer outside, it also costs more, so if you’re painting the outside of your house, for instance, latex paint is often a go-to option. However, acrylic will be your best choice if you want to spend some extra money for added durability.

Regular cleaning, touch-ups for small defects, and resealing or repainting every 2-3 years help to maintain a vibrant appearance and protection.

Typically, a fence requires one to two coats of stain. The exact number can vary depending on the porosity of the wood. For specific guidance, it's best to check the manufacturer's instructions. After applying the first coat and letting it dry completely, you can assess the finish. If it appears patchy, uneven, or you want a more saturated color, a second coat is recommended. An extra coat can also help cover lap marks.

The Oregon, WI homeowners’ guide to painting services

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