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Find Painters in Chestnut Hill

Kennedy Painting
5.0(
108
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Chestnut Hill, 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 rate100%
Recommended by93%of homeowners
Avatar for Olde England Painting
Olde England Painting
5.0(
56
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+5 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1992

Free estimates

Warranties offered

"Paul and his team were absolutely fantastic! They were so courteous and respectful and meticulous in their prep and carpentry work- and we had A LOT of things that needed fixing like rotted windowsills, broken deck stairs, incomplete trim moulding, broken shingles and a crooked garage cupola. They fixed it all! Now my 115 year old house looks so beautiful and I can’t thank Paul and his team enough. They were also so tidy and cleaned up their work areas every afternoon before they left. If you’re considering Olde England Painting just hire them. You will not be disappointed. Last but not least, they were also the most reasonable quote I got and I met with 5 other painters. I would hire them again in a heartbeat!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+4

Response time4 days
Response rate100%
Recommended by100%of homeowners
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 Chestnut Hill, MA and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"Peter and his team did an excellent job! The house needed a lot of carpentry repair (window frames repair, siding replacement etc.) All carpentry work was addressed. All the work was done with high quality. The house looks beautiful and I would recommend North Shore Painting."
Before
After
Exterior
Stairs
Dining Room

+5

Response time2 days
Recommended by96%of homeowners
Quality Preferred Painting
4.7(
90
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+6 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1987

Free estimates

Credit card accepted

"Excellent!! Anthony (foreman) and crew did an exceptional job removing wall paper and painting several rooms in our home. They were professional and meticulous. We would definitely recommend them as well as use them again either for interior or exterior painting."
Exterior Before and After
Exterior Before and After
Exterior Before and After
Sanctuary
Stripping wallpaer

+1

Response time2 days
Recommended by98%of homeowners
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Showing 1-10 of 1727

FAQs for painting projects in Chestnut Hill, 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 Chestnut Hill, MA homeowners’ guide to painting services

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