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Find Painters in Osterville

Avatar for Rainmaker Painting
Rainmaker Painting
4.9(
52
)

Serving Osterville, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2018

Free estimates

Warranties offered

"Rainmaker Painting was fantastic to work with. I met face-2-face with four local painting companies before selecting Rainmaker. Chris and his Team did not disappoint! Fantastic prep work, repaired ceilings, moldings and even an antique front door that needed some attention. All this prep showed in the final results which was a stunning transformation. My wife and I were super impressed with the results after Rainmaker painted our ENTIRE house each room a separate color. The quality of paint and other materials along with Rainmakers experience and attention to detail makes all the difference. We highly recommend Rainmaker Painting, absolutely wonderful experience from start to finish (YES they even cleaned up after themselves :-) too."
Rainmaker Painting 
Interior Painting Specialists 
(617)416-3965
Rainmakerpainting.com
Interior Painting Specialists (617)416-3965 Rainmakerpainting.com
Interior Painting Project
Rainmaker Painting  (617)416-3965
After: Primed with BIN stain blocker/sealer.  Finish Paint is Benjamin Moore, Regal Matte Finish.  Color: Duxbury Grey. Trim is Regal, Semi Gloss. Color: Heron White

+316

Response time7 hrs
Recommended by97%of homeowners
Avatar for Clear Coat Painting
Clear Coat Painting
5.0(
50
)

Serving Osterville, MA and surrounding areas

Approved

In business since 2015

Free estimates

Credit card accepted

House painting. Interior and Exterior. Wallpaper removal. Plastering. Drywall repair. Deck staining. Powerwash. High quality work with affordable prices!!!Deals and discounts on big projects. Senior discount! Special offers during winter!!!

Bar-resturant
Bar-resturant
Bar-resturant
Bar-resturant
Bar-resturant

+68

Recommended by87%of homeowners
Avatar for Schmidt Painting
Schmidt Painting
4.8(
509
)

Serving Osterville, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1997

Free estimates

Emergency services offered

"Schmidt Painting is high quality painting company that I would HIGHLY recomend. Derrick and his crew painted the inside of my house from top to bottom. They have excellent workmanship and were on time everyday. Putting in long hours to make sure the job was done perfectly. We were extermely happy with their skill and their attention to detail. I would defintely recommend Schmidt Painting and would absolutely use them again. 10 + job. If your looking for a painting company look no more.... HIRE Schmidt Painting. You will be happy that you did!!!!"
Schmidt Painting Awards
Schmidt Painting Awards
Schmidt Painting Awards
Schmidt Painting Awards
Schmidt Painting Awards

+20

Response time9 hrs
Response rate100%
Recommended by96%of homeowners
Avatar for Charles Nicholson Painting
Charles Nicholson Painting
4.9(
41
)

Serving Osterville, MA and surrounding areas

Approved

In business since 1999

Free estimates

Small jobs welcome

"Charles painted the second floor of my in-law's new home in Brewster. It was a large room with cathedral ceilings, stained walls and a textured ceiling .as well as a bathroom. His workmanship is top notch; it looks like a new house! He was reasonably priced, prompt, cleaned up at the end of each day and made some recommendations to help make everything look perfect. Would definitely use again and highly recommend him!"
T Jazelle
T Jazelle Showroom
T Jazelle Studio
T Jazelle Main Office
T Jazelle Showroom

+3

Response time5 hrs
Recommended by94%of homeowners
Avatar for Regal Custom Painting, Inc.
Regal Custom Painting, Inc.
4.8(
53
)

Serving Osterville, MA and surrounding areas

Approved

In business since 2014

Free estimates

Credit card accepted

"They stripped the wallpaper in my family room and painted. They were very responsive, scheduled the work promptly and performed the work very quickly and well. I would definitely recommend this company. and, in fact, am already using them for another project."
Response time12 hrs
6 neighbors recently requested a quote
Recommended by97%of homeowners
FCL Painting
5.0(
26
)

Serving Osterville, MA and surrounding areas

Approved

In business since 2000

Free estimates

Customers say: Terrific value

"FCL Painting did an excellent job. Felipe answered my emails when I had additional questions. His crew is hard working. I had walls and ceilings done and they look brand new. They showed up on time, cleaned everything at the end of each day and were just a pleasure to work with."
Response time7 hrs
2 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Anderson & Sons Home Solutions, Inc.
Anderson & Sons Home Solutions, Inc.
4.8(
166
)

Serving Osterville, MA and surrounding areas

Approved

In business since 2012

Free estimates

Warranties offered

"Very professional workers. I am very pleased with theirwork. PAinted my outside trim and stained the deck. Thank you all who recommended them on Home Advisor."
Response time10 hrs
Response rate88%
22 neighbors recently requested a quote
Avatar for A1 Painters
A1 Painters
4.5(
60
)

Serving Osterville, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1999

Free estimates

Emergency services offered

"The team tackled a tough job of a badly deteriorating deck floor and railing. It took several days of sanding to get to a level and smooth surface ready for staining. In addition, they did window trim, fixed pulpy garage door and widow sill areas, power washed house and deck and painting a portion of siding that was peeling. Overall, a good deal of work done after a great prep job."
Moms Deck Replacement
Moms Deck Replacement
Moms Deck Replacement
Moms Deck Replacement
Moms Deck Replacement

+455

Response time1 day
Response rate93%
23 neighbors recently requested a quote
Universal Painting Services, Inc.
4.8(
46
)

Serving Osterville, MA and surrounding areas

Approved

In business since 2010

Free estimates

Customers say: Quality work

"I needed the outdoor trim of my house painted so I went through Home Advisor to see what would come out of that. Andre responded to my need and provided me with a very professional quote. I selected his company to do the work and I am extremely glad I did. These guys went above and beyond to deliver excellent work. I was a bit nervous as I was coming up against the Holidays and needed to get this work completed quickly. His team showed up very early AM daily and worked until sunset. This was a challenging job to ensure the trim next to newly installed shingles was meticulously painted. They met the challenge!! All other trim work was equally well done!! My wife and I are super impressed and would recommend them in a heartbeat. If you need painting done you will not be disappointed."
Interior Painting
Interior Painting
Interior Painting
Interior Painting
Interior Painting

+17

Response time1 day
Recommended by100%of homeowners
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Showing 1-10 of 474

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

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