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Find Painters in Winthrop

Avatar for Erivan Da Silva Painting
Erivan Da Silva Painting
4.8(
70
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+16 more

Serving Winthrop, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1997

Free estimates

Warranties offered

"Erivan and his team were super responsive and responsible and great to work with. They did really high quality work for us, and I loved the result. They have been painting for years, and were referred to me from a friend who had them paint his historic Somerville home with many details. The team was always on time, and they were great problem solvers when things inevitably came up (we ran out of paint, for example). I was also impressed that they painted all the trim perfectly without painters tape :) Their work included doing some light spackling of wall cracks, and removal of shades before they started. Finally, they were super fast!"
Painting - Exterior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project

+846

Response time1 day
Recommended by93%of homeowners
Avatar for ARCH PAINTING
ARCH PAINTING
4.4(
161
)
Interior Painting or Staining: 5 + RoomsExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+14 more

Serving Winthrop, MA and surrounding areas

Approved

In business since 1997

Free estimates

Warranties offered

"Work was performed exactly as discussed and agreed to (match existing paint colors) at estimated cost. Start was delayed at our request due to high heat and humidity, with no complaints. Work was further delayed through no fault of Arch Painting due to continuous wet weather. Once a good weather window finally occurred, the work was performed quickly with no impact on us. We were totally satisfied with the quality of the work and the finished product."
BEFORE
AFTER
Before
After
Before

+17

Response time12 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for North Shore Painting
North Shore Painting
4.8(
59
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Winthrop, MA and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"Our three-story Victorian needed exterior painting and repair work (siding, trim, porch), and as with many Victorians, had a lot of detail work. The team from North Shore did a fantastic job - they were thorough, fast for such a large project, and respectful of our property. The team's attention to detail was extraordinary - before the last day of work, we did a walk around to make note of the handful of items that we saw that we wanted to make sure got done. Without us even needing to mention those to the team, they addressed every single one as part of their final touch up process. This level of attention to detail is not something we have had from all contractors we have worked with. We would absolutely use North Shore again for future projects. Pricing was fair, but not cheap - that said, you get what you pay for and the quality speaks for itself."
Before
After
Exterior
Stairs
Dining Room

+5

Response time2 days
Recommended by96%of homeowners
Avatar for VanGuard Pro Painters
VanGuard Pro Painters
5.0(
96
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Building - Paint or Stain - For Business+1 more

Serving Winthrop, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2017

Free estimates

Emergency services offered

"This company repainted two warehouse units I own and did a great job. I have done some internal house painting myself so I can appreciate the fine job- good straight lines between paint of different colors on wall and ceiling, even quality paint coverage, just generally first rate. Would recommend."
Carp & Painting Projects
Residential Exterior Painting
Residential Exterior Painting
Residential Exterior Painting
Front Porch

+83

Response time2 days
8 neighbors recently requested a quote
Recommended by60%of homeowners
Star Painting Service Group, Inc.
5.0(
30
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Building - Paint or Stain - For Business+2 more

Serving Winthrop, MA and surrounding areas

Approved

In business since 2007

Free estimates

Offers commercial services

"They are hard working and clean up everything. The crew were excellent and very polite. I would recommend Star Painting for anyone who is considering painting their house. They even did needed carpentry. Our home has never looked so good on the outside since we bought it in 2008. Thank you Eddie and the Star Painting Crew!!!!!!"
2 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for R & N Painting
R & N Painting
5.0(
25
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Winthrop, MA and surrounding areas

Approved

In business since 2016

Free estimates

Customers say: True professional

"Ryan was great. Heâ  s a â  no dramaâ  kind of guy. Showed up when he said he would. Explained things clearly. Respected my needs and scheduling. Was accommodating about fitting in the work over time as there were a lot of touch-ups to do left over from former contractors or changes in the house. As a single woman I felt comfortable being alone with him in my house. He was never inappropriate, focused on doing the work and wasnâ  t crazy-rushed. He took his time and was friendly. Great experience. Oh, yea, good paint job too!"
Woburn finished
Woburn
Woburn 1
Woburn 2
Jamaica Plain porch remod

+23

Response time4 hrs
Response rate98%
3 neighbors recently requested a quote
Good To Go Painting
4.5(
42
)
Exterior or Interior Surfaces - Paint RemovalInterior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms+1 more

Serving Winthrop, MA and surrounding areas

Approved

In business since 2000

Customers say: Quick response

"I would highly recommend this company. Donald and his crew were very flexible and easy to work with. They provide very reasonable prices for excellent work. They went above and beyond just painting the house. I would call them again for future projects!"
Replace wood fence and paint
Replace wood fence and paint
Replace wood fence and paint
Build new deck
Built new deck

+15

Response time2 days
Recommended by100%of homeowners
Avatar for Urbano Painting, Inc.
Urbano Painting, Inc.
4.9(
24
)
Interior Painting or Staining: 5 + RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Surfaces - Paint or Stain- For Business

Serving Winthrop, MA and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"I highly recommend Urbano Painting. They applied solid stain to the cedar siding and trim of our two-story colonial and performed some repair and replacement carpentry - at a price that was lower than all but one of the quotes I received. All of their work was impeccable. Jocimar and his whole team are a pleasure to deal with and went the extra mile to ensure our complete satisfaction. Everything was done with a high degree of professionalism, from prep work to staining to daily cleanup. The whole experience exceeded my expectations, and I hope to hire them again for interior painting."
painting
painting
painting
painting
painting

+24

Response time4 hrs
Response rate89%
1 neighbors recently requested a quote
...
Showing 1-10 of 1419

FAQs for painting projects in Winthrop, MA

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 Winthrop, MA homeowners’ guide to painting services

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