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Top-Rated Deck staining pros in Jamaica Plain - Updated Nov 2026

Avatar for Olde England Painting
Olde England Painting
5.0(
56
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 1992

Free estimates

Warranties offered

"We have used Olde England to paint both the interior and exterior of our old Victorian house. They do a terrific job and we would highly recommend them. They are professional, hard working, and keep a clean workspace. They’ve also done several carpentry repairs that were well done."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+4

Response time4 days
Response rate100%
Recommended by100%of homeowners
Kennedy Painting
5.0(
109
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium

Serving Jamaica Plain, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1990

Free estimates

Emergency services offered

"I highly recommend Kennedy Painting! Brain (the owner) was very personable and provided excellent customer service. When we walked around my house to going over what work needed to be done, he asked a lot questions and gave me some advice about different projects around the house. He also provided more than one estimate, so that we have different options to which we could choose from. Brian’s crew worked efficiently and did an excellent job with our exterior trim and deck. They scraped, sanded, primed and painted the trim of our house and sanded and painted our deck, not only to make it look better, but to preserve it for years to come. Thank you Kennedy Painting!"
Response time1 day
Response rate100%
Recommended by92%of homeowners
Avatar for Foxrock Painting, LLC
Foxrock Painting, LLC
5.0(
74
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 2017

Free estimates

Warranties offered

"This company is exceptional. They have great customer service. Their workers/painters were courteous, professional and did a great job doing carpentry and staining my deck. I would hire them again in a heartbeat. They are a wonderful family run business."
Archway Entrance - AFTER
Front Entrance - AFTER
Side View - AFTER
Entire House - AFTER
Side Steps - AFTER

+62

Response time1 day
Response rate91%
12 neighbors recently requested a quote
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

Serving Jamaica Plain, MA and surrounding areas

Approved

In business since 1987

Free estimates

Credit card accepted

"This was our second time hiring Quality Preferred to do prep and paint for the interior of a house prior to move in. Would absolutely use again for future projects. High quality work and attention to detail, professional demeanor, work done on schedule, and good customer service. If you want to make sure job is done right, go with them."
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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Deck Staining FAQs, answered by experts

You don’t necessarily have to remove all the old paint before repainting your deck, but it’s best to remove as much as possible to ensure a smooth and long-lasting finish. Prioritize scraping off loose, peeling, or flaking paint, and sand down rough areas to create a smooth surface for the new paint to bond with.

An exterior paint job typically lasts between 5 and 10 years, though this can range from 3 to 17 years depending on several factors. The longevity is influenced by the quality of the paint and primer, the quality of the application, the local climate, and the type of surface being painted. For example, paint on wood siding may need to be redone every 3 to 7 years, while painted brick can last up to 17 years. Aluminum siding often needs repainting every 5 years.

Whether you can paint over your existing paint depends on what’s on there. Most of the time, you’ll want to sand down or scrape off the paint that’s currently coating your surface. Epoxy paint, for example, won’t let new paint stick to the surface. Latex paint is more forgiving and will accept a new coat, but a primer is recommended if you’re switching colors.

Stain is meant to be absorbed by the porous wood, allowing some of the natural grain to show through. With that in mind, you don’t want to add more stain than the wood can absorb, as you risk covering up its natural markings. Generally, two coats is the maximum you should do, although very dense hardwoods may only be able to take a single coat.

By applying protective finishes and using durable materials that withstand weather and time.

The Jamaica Plain, MA homeowners’ guide to deck staining services

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