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Top-Rated Painters in Old Greenwich - Updated Nov 2026

Avatar for J & S Painting Plus Inc
J & S Painting Plus Inc
4.7(
335
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 1977

Free estimates

Warranties offered

"We had our exterior of our house painted and the deck stained. Jay took the time to explain the whole process and answered all of our questions (and we had a lot of questions!). The detailed quote outlining all of the work to be done was excellent and helped us understand what exactly was going to be done. It is clear he takes pride in the work that he and his teams do. There was open communication throughout the process and the job was very well done. Jay, Jose, and the crew were professional and the results of the job clearly demonstrates that."
Additional Photos
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Before & After
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+3

Response time1 day
Recommended by94%of homeowners
PB Painting
4.6(
59
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+4 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 1998

Free estimates

Warranties offered

"Lightening fast response to my inquiry on Home Advisor by Pablo of PB Painting. Pablo is highly consultative, confident, knowledgable, professional and very friendly. A+++++ Rating by these homeowners! Highly recommend PB Painting !"
entrance
 patio
entrance
 finish
 patio

+16

Response time7 hrs
Response rate91%
Recommended by71%of homeowners
Avatar for All Painting Decoration Corp
All Painting Decoration Corp
4.9(
46
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+5 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 2005

Free estimates

Emergency services offered

"Junior and his guys exceeded our expectations!  My husband and I could not be happier with their painting job of our bedroom.  We put off painting the bedroom because we thought that the price would be outrageous - it's a very large room with super high ceilings.  But we decided to shop around.  We had more than five painters come by to give us quotes.  When Junior showed up, we could tell that he was a pro but also easy going - how someone is when they are confident about their work.  We decided to go with him.  He confirmed the start date days in advance and showed up when he promised.  The work took exactly as long as he said it would.  It's not an easy room - height of ceilings, tons of white beams.  Not a speck of slate blue paint where it should not be and the room is as clean now as it was when they arrived.  They prepped the walls beautifully.  The painting around the white beams, ceiling and baseboards is perfect.  Did I say that we're super happy!  Thank you Junior and your team for being very reasonably priced, proficient, neat, courteous, and respectful.  I highly recommend All Painting Decoration Corp!  "
Additional Photos
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Additional Photos

+25

Response time2 days
Response rate100%
Recommended by100%of homeowners
Avatar for Edge Painting
Edge Painting
5.0(
44
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Medium+1 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 2005

Free estimates

Warranties offered

"I hired these folks for a challenging interior job that required repair of old plaster walls and painting over very old paint. Things went well and I was happy with the work as well as the cleanliness of the overall process. I would recommend to anyone looking."
Weston job
Weston Ct
Weston CT
Weston CT
Weston CT

+108

Response time1 day
Response rate91%
2 neighbors recently requested a quote
Avatar for NHV Painters and Flooring
NHV Painters and Flooring
4.9(
96
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+12 more

Serving Old Greenwich, CT and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Credit card accepted

"Glenn and his team did an AMAZING job painting the interior of my house. They were able to answer any questions that I had about the project and finished the job on time. My house looks better than ever! I will definitely hire New Haven Painters again for any future painting projects."
Exterior Painting
Interior Painting
Cabinet Refinishing
Commercial Painting
Painters In Action!

+118

Response time2 hrs
Recommended by43%of homeowners
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FAQs for painting projects in Old Greenwich, CT

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 Old Greenwich, CT homeowners’ guide to painting services

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