Top-rated painters.

Get matched with top painters in Winthrop, MA

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Top-Rated Painters in Winthrop - Updated Nov 2026

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+3 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(
162
)
Interior Painting or Staining: 5 + RoomsInterior Painting or Staining: 3 - 4 RoomsExterior Building - Paint or Stain - For Business+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%
3 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 The Painter
The Painter
4.9(
59
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms

Serving Winthrop, MA and surrounding areas

Approved

In business since 2002

Free estimates

Offers commercial services

"Bill was very professional repaired some places on the house I did not know needed to be repaired. His paint job was excellent and my house sold fast because it looked so good. He was polite and on time for the jobs"
Various jobs
Various jobs
Various jobs
Various jobs
Various jobs

+2

1 neighbors recently requested a quote
Recommended by94%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
4 neighbors recently requested a quote
Recommended by60%of homeowners
Avatar for R & N Painting
R & N Painting
5.0(
25
)
Interior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 5 + Rooms

Serving Winthrop, MA and surrounding areas

Approved

In business since 2016

Free estimates

Customers say: True professional

"Ryan did an excellent job painting my bedroom and den. He was easy to work with and was prompt each day to work. He did exactly what I wanted and more including some carpentry. He did an excellent cleanup each day and worked until each day was complete. I would recommend Ryan to anyone who needs painting. A good guy an an excellent painter. I would hire him again in an instant."
Woburn finished
Woburn
Woburn 1
Woburn 2
Jamaica Plain porch remod

+23

Response time4 hrs
Response rate98%
1 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

"Donald listened to my concerns and answered all questions before I hired him. He phoned as needed to confirm all appointments & schedule changes. He worked carefully & meticulously on my fussy window trim project. I would recommend his skills on other household projects without any hesitation at this house and my rental property."
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 G&M Painting and Cleaning, Inc.
G&M Painting and Cleaning, Inc.
4.7(
14
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or Stain: Medium

Serving Winthrop, MA and surrounding areas

Approved

In business since 2008

Free estimates

Warranties offered

"G&M did a wonderful job on my kitchen cabinets. They supplied the paint, while I supplied the handles and hinges I liked. The job was quoted and completed in a timely manner by this father and son company. There was a bit of overspray, however I saw how well that they had taped off the areas and knew that it was not by an oversight. When the hinges I selected did not align perfectly, they spent the extra time to make sure that they would still look great. I am very happy with out the kitchen came out. I would definitely recommend G&M for painting jobs."
stained Cabinets
Repainted Cabinets
Repainted Cabinets
Repainted Cabinets
Repainted Cabinets

+5

Response time8 hrs
2 neighbors recently requested a quote
Recommended by90%of homeowners
...
Showing 1-10 of 1430

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.