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Find Painters in Winter Park

Avatar for Kingdom Painting
Kingdom Painting
4.9(
278
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Home or Structure - Paint or Stain

Serving Winter Park, FL and surrounding areas

Approved

Super Service Award Winner

In business since 2005

Free estimates

Warranties offered

"Professional and courteous paint crew and most importantly great paint job Good attention to detail, sanding and prepping as required and they put everything back, ie gutter and motion lights. I highly recommend as they even paint lower along the bottom to show consistently of new paint color. They take pride in their work and rightfully so."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+15

Response time9 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for Stunning Contractor Solutions, LLC
Stunning Contractor Solutions, LLC
5.0(
20
)
Interior Painting or Staining: 5 + RoomsExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+5 more

Serving Winter Park, FL and surrounding areas

Approved

Super Service Award Winner

Free estimates

Warranties offered

Credit card accepted

"Amanda and her team did an amazing job painting our house, and we're so happy we chose this company. Amanda was incredibly friendly and supportive in helping us understand what would be involved. She was up front about the challenges of bold yellow as an exterior paint (the only complaint I have is how difficult Sherwin Williams' website is for choosing a color because you can't filter colors by paint type, but that's not Amanda's fault). This is an older house repaint, not a new build, and they knew what they were doing for it. The painter team, Kevin and Dennis, were highly skilled and worked very quickly. And they were so happy--singing, laughing and joking while they worked --it felt like our house was being covered in joy as well as a beautiful new paint job! Amanda checked in throughout the process, and it's clear she and her team respect each other. All in all we are delighted with this company and will use them again for future paint needs!"
Garage Epoxy
Epoxy Flooring Project
Garage Epoxy
Epoxy Flooring Project
Garage Epoxy

+43

Response time7 hrs
Response rate100%
1 neighbors recently requested a quote
Avatar for J & C Coatings
J & C Coatings
5.0(
35
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+12 more

Serving Winter Park, FL and surrounding areas

Approved

Super Service Award Winner

In business since 1999

Free estimates

Emergency services offered

"Jim was friendly, quick to respond, and efficient. We are very grateful for the work his team completed and that they were able to complete it much sooner than we originally expected. The painters did an excellent job painting our walls and trims. Will definitely hire them again for future painting needs."
Painting - Interior Project
Painting - Interior Project
Painting - Exterior Project
Painting - Exterior Project
Painting - Exterior Project

+21

Response time7 hrs
Recommended by78%of homeowners
Lazaro's Painting Service, Inc
4.7(
116
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or Stain: Medium+3 more

Serving Winter Park, FL and surrounding areas

Approved

In business since 2000

Free estimates

Credit card accepted

"Lazaro and his team did a wonderful job painting my home! He was very communicative, fairly priced, and especially efficient. I’d happily have him back for more work and highly recommend his services!"
10 neighbors recently requested a quote
Recommended by93%of homeowners
D&S Painting & Power Washing
4.8(
54
)
Metal Roofing - Paint

Serving Winter Park, FL and surrounding areas

Approved

In business since 2015

Free estimates

Customers say: Quick response

"I had Sam paint two porches, one concrete front porch that needed significant prep work (power washing and etching) and the other a wooden side porch. Sam responded immediately to my job request and came out the same day to do the estimate. The price was very competitive, and Sam did a great job evaluating what we needed to do and explaining his recommendations and all the details of the process. He did the job over the weekend and it is exactly what we needed--fresh and clean and ready for the fall. I would definitely hire him again."
blum project
blum project
blum project
blum project
blum deck

+39

Response time2 hrs
Response rate89%
Recommended by97%of homeowners
Avatar for Roll City Painting Orlando LLC
Roll City Painting Orlando LLC
4.8(
57
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Medium

Serving Winter Park, FL and surrounding areas

Approved

In business since 2000

Free estimates

Warranties offered

Roll City Painting is a professional residential and commercial painting company proudly serving Orlando, Windermere, Winter Garden, Winter Park, Lake Nona, Clermont, Lake Mary, and surrounding Central Florida communities.\n\nWe specialize in interior and exterior painting, stucco painting, cabinet refinishing, commercial painting, wallpaper removal, popcorn ceiling removal, and staining services.\n\nOur team is committed to exceptional craftsmanship, clear communication, detailed preparation, and a smooth experience from estimate to final walkthrough. We use premium Sherwin-Williams products and proven painting techniques to deliver beautiful, long-lasting results.\n\nWhether you're refreshing your home's interior, protecting your stucco exterior, or transforming your business, Roll City Painting is ready to help. Contact us today for your free painting estimate!

Stucco Exterior Project
Stucco Exterior Project
Stucco Exterior Project
Stucco Exterior Project
Stucco Exterior Project

+4

3 neighbors recently requested a quote
Recommended by88%of homeowners
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FAQs for painting projects in Winter Park, FL

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 Winter Park, FL homeowners’ guide to painting services

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