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Top-Rated Painters in South Windham - Updated Nov 2026

Avatar for J&L Finishes, LLC
J&L Finishes, LLC
5.0(
30
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+5 more

Serving South Windham, ME and surrounding areas

Approved

In business since 2005

Free estimates

Warranties offered

"I hired Lenzen Pro Painting to paint the exterior of my home along with some stucco repair. They did a fantastic job. I am very happy with the results. Everyone at Lenzen is a pro at their jobs. I received a detailed itemized estimate which none of the other companies I got estimates from did. The person who prepped my house was thorough to prevent over-spray and catch any drips. The stucco repairs came out much better than I thought they could and after painting it's very hard to tell where any repairs had been done. Oscar, the person who prepped my house and did the repairs, also painted my house. It was done very professionally. Small imperfections and problems areas around the exterior have completely vanished. My home looks great. I will use this company again for my future painting projects. I recommend this company for its professionalism, great communication throughout the project and, quality results."
Hallway brush work
detailed brush work around items
All item covered prior to paint
After pic
Painting over stairs

+30

Response time1 day
Recommended by90%of homeowners
Avatar for Avid Painting LLC
Avid Painting LLC
5.0(
10
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving South Windham, ME and surrounding areas

Approved

In business since 2023

Free estimates

Warranties offered

"Alic did an amazing job, he showed up every day that the weather cooperated in order to get the job done in a timely manner. The deck was unfinished wood prior to him coming and now it looks incredible! We would definitely hire him again for any other painting needs, interior or exterior!"
Exterior Painting Project
Project 6/27/2023
Exterior Painting Project
Project 6/27/2023
Exterior Painting Project

+26

Recommended by100%of homeowners
Avatar for Redo Properties
Redo Properties
5.0(
51
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+7 more

Serving South Windham, ME and surrounding areas

Approved

In business since 1995

Free estimates

Credit card accepted

"Tux previously painted the exterior of another property we own. We had bought the new property and it was in need of a major paint job - basically the entire interior. The current paint colors were all very dark and there was significant detail work to be done with things like board and batten, built ins and, pine beams and v-groove. This was a home my wife and I decided we were going to get exactly right. As before, Tux did a detailed walkthrough, provided a thorough estimate and followed through with the exceptional work we've come to expect from him. High quality paint, craftmanship and a do it until it's right attitude produces a great product."
Painting - Interior Project
5th job- this client
Painting - Interior Project
Before
Before

+266

Response time8 hrs
Response rate100%
Recommended by78%of homeowners
By the Numbers Painting
4.6(
84
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms

Serving South Windham, ME and surrounding areas

Approved

In business since 2008

Free estimates

Customers say: Quick response

"James is such a pleasant person to have around while heâ s working on improving your home. He is great with communicating and planning. He cleans up at the end of each day. He does a fantastic paint job. He shows up on time every day."
Facelift ... Please
Facelift ... Please
Results ... Beautiful
Results ... Beautiful
Results ... Beautiful

+1

Response time4 hrs
Response rate89%
Recommended by88%of homeowners
Avatar for Afterwalls Painting
Afterwalls Painting
5.0(
12
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+1 more

Serving South Windham, ME and surrounding areas

Approved

Super Service Award Winner

In business since 2024

Free estimates

Offers commercial services

"Ben and Afterwalls Painting were phenomenal to work with! We hired them to do a light restoration and stain on our deck. Ben was courteous, efficient, left his work site clean and tidy, and did an awesome job! If you’re looking for a fair, honest, quality local contractor to do finishing work, I highly recommend Ben and Afterwalls Painting! 100/100 A+++"
Deck painting
Deck painting
Deck painting
Full house
Full house

+7

Response time2 days
Response rate94%
Avatar for Myatt & Son Painting
Myatt & Son Painting
5.0(
8
)
Exterior Home or Structure - Paint or Stain: LargeExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+9 more

Serving South Windham, ME and surrounding areas

Approved

In business since 2000

Free estimates

Credit card accepted

"Shawn Myatt and his son, Ethan, were great and did a great job painting two sides of our big old farm house. Shawn is a very conscientious, hard, worker. Polite. Friendly. Respectful. Easy to work with, discussing various aspects of the project. Shawn treated it like it was his own home!"
Mansion Barn
Mansion Barn
Mansion Barn
Mansion Barn
Mansion Barn

+16

1 neighbors recently requested a quote
Recommended by50%of homeowners
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Showing 1-10 of 329

FAQs for painting projects in South Windham, ME

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 South Windham, ME homeowners’ guide to painting services

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