Top-rated painters.

Get matched with top painters in Jamaica Plain, 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.

Find Painters in Jamaica Plain

Avatar for Erivan Da Silva Painting
Erivan Da Silva Painting
4.8(
68
)

Serving Jamaica Plain, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1997

Free estimates

Warranties offered

"I recently hired Erivan for the first time to paint two rooms in my condo. He and his team did excellent work in a diligent and timely manner and at a very reasonable price. I will definitely hire him again and recommend him to anyone I know who needs painting done."
Painting - Exterior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project

+846

Response time10 hrs
1 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for Keane Painting
Keane Painting
5.0(
104
)

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 2001

Free estimates

Customers say: True professional

"Barry and Paul were wonderful! Not only did they give us the best price, but they picked up the exact paint we chose and that was included. Additionally, they were prompt, friendly, and did an impeccable job with painting the room - we will definitely be working with Keane Painting again and would HIGHLY recommend!!"
Response time1 day
Response rate95%
2 neighbors recently requested a quote
Avatar for High Definition Painting Inc
High Definition Painting Inc
4.9(
86
)

Serving Jamaica Plain, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Credit card accepted

"High Definition Painted the entire interior of my home 12 plus rooms. My Wife and I are extremely happy with the results. We also had High Definition paint the exterior of my home several years ago and were very happy with the results. Would highly recommend this Company and will call them for future painting jobs."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+32

Response time8 hrs
Response rate91%
1 neighbors recently requested a quote
Kennedy Painting
5.0(
108
)

Serving Jamaica Plain, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1990

Free estimates

Emergency services offered

"Brian and his team were great. Not only did they do a great job painting, but Brian had us leave all furniture in place and his team moved it to paint and moved it back in place before we got home. Extremely helpful for those of us that don't have time to be rearranging furniture morning and night. They also assisted determining where some stains were coming from by removing drywall and replacing it, in an awkward area of the ceiling. They repaired and looked like new. Highly recommend Brian and his team."
Response time1 day
Response rate92%
1 neighbors recently requested a quote
Avatar for Olde England Painting
Olde England Painting
5.0(
56
)

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 1992

Free estimates

Warranties offered

"Olde England Painting is amazing! They were what every home owner dreams of for repairs. I hired them for painting my house (2 story dutch colonial) which sorely needed a lot of work with peeling paint and rotted wood in several places. Their quote was a bit lower than the highest I had but Paul Adkins was so very professional and explained every step and the materials he would use so well that I was convinced he would be a good choice - and he absolutely was. Paul and his crew exceeded my expectations. The job took 7 days and each day they cleaned up in the evening and set up promptly the next morning. The cleaning, priming, wood repairs, painting, trim were all done perfectly. They even found when replacing a board on the porch that behind it was a wooden medallion that had been hidden for decades. After showing me they renovated the whole thing and painted it to look like beautiful brass at no additional charge. Further, after seeing the great job they did on cleaning the house cedar shingles, I asked them to do my wood deck which they did beautifully. Paul suggested a sealant that has made the deck look completely new. In hind sight the cost was the best money I have spent in many years and unquestionably the best work I have ever had done. No delays, exceptionally skillful, and truly professional."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+4

Response time5 days
1 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for ARCH PAINTING
ARCH PAINTING
4.4(
160
)

Serving Jamaica Plain, 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
5 neighbors recently requested a quote
Recommended by88%of homeowners
Avatar for Supreme Painters Inc
Supreme Painters Inc
4.9(
116
)

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 2007

Free estimates

Emergency services offered

"Supreme Painting did an awesome job and in less time than originally estimated. They were also easy to communicate with, professional, and responsive. I would hire them again in the future."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+52

Response time2 days
Recommended by97%of homeowners
Avatar for North Shore Painting
North Shore Painting
4.8(
59
)

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"My crew from NSP was amazing. Professional, courteous, kind and on point to get the task done. Large 2 story colonial with addition and ovs garage. I believe it took total of 5 days because of early weather in October 22. No paint chips on ground, very conscious of my shrubs and gardens, you would not even know they were painting. I HIGHLY RECOMMEND this outstanding company and would not hesitate to have them paint my home again. The price was very fair, the warranty good but most of all they always stayed in touch to let me know what was going to happen etc. My team, Frank, Benjamin and Valerio were amazing. Peter the owner and coordinator did a great job. Thank you again. My neighbors stopped to tell me how great my home looks and asked for the name of the painters for them in springtime. Thats says much about Northshore Painting. Great job, great professionalism, great job. VCM Billerica Ma"
Before
After
Exterior
Stairs
Dining Room

+5

Response time2 days
2 neighbors recently requested a quote
Recommended by96%of homeowners
Quality Preferred Painting
4.7(
90
)

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 1987

Free estimates

Credit card accepted

"Steve and his crew do exceptional work - professional, reliable, conscientious and top quality. It is obvious that they care about the quality of their work and they understand that the key to a good paint job is preparation and attention to detail. Steve's crew worked extremely hard to prepare my home to accept its latest coat of paint, and the results speak for themselves as they produced a nearly flawless job. I have had my house painted 3 or 4 times over the years and Steve's work was by far the best - not even close. You cannot go wrong with these guys."
Exterior Before and After
Exterior Before and After
Exterior Before and After
Sanctuary
Stripping wallpaer

+1

Response time3 days
Recommended by98%of homeowners
Avatar for Boston Painting Services Inc.
Boston Painting Services Inc.
4.9(
109
)

Serving Jamaica Plain, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2002

Free estimates

Emergency services offered

"Cassio and his team painted two closets and two ceilings for us. We were very pleased with the quality of the work and plan to contact Cassio for our next project. We would highly recommend Boston Painting Services."
Carpentry - Woodworking Project
Painting - Exterior Project
Additional Photos
Additional Photos
Additional Photos

+79

Response time3 days
Response rate92%
Recommended by92%of homeowners
...
Showing 1-10 of 1940

FAQs for painting projects in Jamaica Plain, 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 Jamaica Plain, MA homeowners’ guide to painting services

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