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Find Painters in Windsor

Avatar for Edwin Ingraham Paintings
Edwin Ingraham Paintings
4.8(
36
)

Serving Windsor, ME and surrounding areas

Approved

In business since 2013

Free estimates

Warranties offered

"Edwin (aka Cappy} was hired to paint and provide carpentry service for my 1885 family home in Friendship, Maine. The home has been in the family for generations and is very special to us. Cappy and his crew scraped, primed and painted the main house as well as provided carpentry as needed. His crew resheathed, shingled and stained 3 outbuilding and repaired thresholds and trim on the same. the house is on an island so the logistics were complicated. Cappys crew accomplished all of the work in less than two weeks and the results exceeded my expectations. I will hire them again when needed, you should too."
Doorway
Ceiling
After Painting
Hallway
Staircase

+4

Response time5 hrs
Response rate93%
17 neighbors recently requested a quote
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Avatar for Fine line painting
Fine line painting
5.0(
10
)

Serving Windsor, ME and surrounding areas

Approved

In business since 1990

Warranties offered

Small jobs welcome

"Don and his crew were pleasant, professional, showed up on time and communicated well with me during the project. He did a great job prepping my garage floor for epoxy painting and clear coat application. He pays attention to detail, answered any questions I had and cleaned up after working. His services are fairly priced and I highly recommend him and his crew! I liked his work so much I've hired him to prep and paint my deck!"
Living room
Project One
Project One
Project One
Project One

+8

Response time7 hrs
Response rate100%
50 neighbors recently requested a quote
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Avatar for True North Roofing
True North Roofing
5.0(
23
)

Serving Windsor, ME and surrounding areas

Approved

Super Service Award Winner

In business since 2022

Free estimates

Emergency services offered

"I had a great experience with this company, I highly recommend True North Roofing, not only for my projects but also to my painting customers that are seeking a roofing professional, quality products and excellent service."
1
2
3
4
5

+17

Response time1 day
Response rate92%
41 neighbors recently requested a quote
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Avatar for DP Painting
DP Painting
5.0(
4
)

Serving Windsor, ME and surrounding areas

Approved

Super Service Award Winner

In business since 2024

Free estimates

Small jobs welcome

"Did a great job. Built mailbox stand with an excellent custom flair. Built for strength. Texted and came right away. The message transition to know who was talking to me was confusing at first. DP was also not sure who it was initially."
Interior
Interior
Entryway
Entry
Jobs

+12

Response time3 hrs
Response rate88%
40 neighbors recently requested a quote
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Avatar for L&B Services
L&B Services
5.0(
15
)

Serving Windsor, ME and surrounding areas

Approved

In business since 2014

Free estimates

Warranties offered

"Bob and his crew installed a fence on my property. They were great. They did a beautiful job, were professional and kind. We would definitely hire him again."
Before
After
before
after
Response time12 hrs
7 neighbors recently requested a quote
Recommended by46%of homeowners
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Avatar for The Golden Rule Handyman, LLC
The Golden Rule Handyman, LLC
4.4(
32
)

Serving Windsor, ME and surrounding areas

Approved

In business since 2013

Free estimates

Emergency services offered

"Mike was very pleasant and did a wonderful job painting my bathroom. Also put up some trim in entranceway. I have more work that needs to be done and will be calling him."
Response time2 days
Recommended by96%of homeowners
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Avatar for Innovative Construction
Innovative Construction
3.7(
32
)

Serving Windsor, ME and surrounding areas

Approved

In business since 2015

Free estimates

Emergency services offered

"This team was very efficient, clean and got the job done well. Will certainly use this crew for future projects"
Before
Deck Repair
Deck Repair
Before
MIDWAY

+6

Response time3 days
13 neighbors recently requested a quote
Recommended by45%of homeowners
Request Quote
...
Showing 1-10 of 202

FAQs for painting projects in Windsor, 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 Windsor, ME 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