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Top-Rated Painters in Cottage Grove - Updated Nov 2026

Avatar for Five Star Painting of Madison WI
Five Star Painting of Madison WI
4.8(
196
)
Interior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or Stain: Small+4 more

Serving Cottage Grove, WI and surrounding areas

Approved

Super Service Award Winner

In business since 2016

Free estimates

Warranties offered

"This was our first experience with hiring 5 5tar Painting and have hired other paintings contractors before. 5 Star Painting showed us a whole new level of professionalism, organization and workmanship. They definitely live up to there name 5 Star and will not consider any other paintings contractor again."
Before and After
Before and After
Before and After
Before and After
Before and After

+574

Response time4 hrs
20 neighbors recently requested a quote
Recommended by92%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: LargeExterior Home or Structure - Paint or Stain: Medium+1 more

Serving Cottage Grove, 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 Ultra Painting, LLC
Ultra Painting, LLC
4.9(
20
)
Interior Painting or Staining: 3 - 4 RoomsExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+4 more

Serving Cottage Grove, WI and surrounding areas

Approved

In business since 2019

Free estimates

Warranties offered

"I had a crew from Ultra Painting stain my exterior & paint the window frames and they did a wonderful job! They were very meticulous with a display of high quality & perfection! I will likely reach out to them for future home improvement jobs at my house!"
Ceiling Repaint
Master Bedroom
Living Room
Living Room
Kitchen

+15

Response time1 day
Response rate96%
12 neighbors recently requested a quote
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+2 more

Serving Cottage Grove, 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%
Avatar for 4 Lakes Painting, LLC
4 Lakes Painting, LLC
4.9(
9
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Home or Structure - Paint or Stain: Small+2 more

Serving Cottage Grove, 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 ALL TRADES PAINTING & REMODELING LLC
ALL TRADES PAINTING & REMODELING LLC
5.0(
3
)
Exterior Home or Structure - Paint or Stain: MediumExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+2 more

Serving Cottage Grove, WI and surrounding areas

Approved

In business since 2021

Free estimates

Credit card accepted

With several years experience, we work hard to bring each customer the best possible service and quality available. We look forward to working with you on your next project. We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer’s needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job. We welcome your questions and thank you for your interest. Call today!

4 neighbors recently requested a quote
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Showing 1-10 of 287

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

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