Top-rated painters.

Get matched with top painters in Winter Park, FL

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Painters in Winter Park

Avatar for Kingdom Painting
Kingdom Painting
4.9(
274
)
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 G & M GENERAL PAINTING INC
G & M GENERAL PAINTING INC
5.0(
21
)
Painting or Staining - Small ProjectsInterior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or Stain: Medium+9 more

Serving Winter Park, FL and surrounding areas

Approved

In business since 2024

Free estimates

Credit card accepted

"I was very pleased with the job Brayan did, painting our hallway. Even though we had the whole inside of the house painted last year, the hallway looked terrible. It drove me crazy for almost a year. I wish I had called Brayan sooner. He said it needed repainted. He gave recommendations on the paint to use for the best results and even purchased the paint before coming to do the job. Brayan even painted an extra wall that I had not thought about, and didn't charge me anything more than the estimate he had given initially. Brayan was very nice and professional. I will definitely use him for all my painting needs in the future."
Kitchen Cabinets Painting
Kitchen Cabinets Painting
Kitchen Cabinets Painting
Kitchen Cabinets Painting
Kitchen Cabinets Painting

+26

Response time4 hrs
Response rate100%
13 neighbors recently requested a quote
Lazaro's Painting Service, Inc
4.7(
115
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms+3 more

Serving Winter Park, FL and surrounding areas

Approved

In business since 2000

Free estimates

Credit card accepted

Since 2000, Lazaro?s Painting Service, has been able to provide the Orlando and surrounding areas with unmatched painting service. Customer preference and priorities are always first with us and we're very timely with our work and never lose attention to detail. Lazaro's Painting Service, has built a reputation for quality work with each satisfied customer. Our sense of pride is apparent in every restoration we complete. Give us a call today, we are excited to hear more about your project and look forward to earning your business.

25 neighbors recently requested a quote
Recommended by94%of homeowners
Avatar for Bobs Painting & Coatings LLC
Bobs Painting & Coatings LLC
4.9(
52
)
Exterior Home or Structure - Paint or Stain: SmallExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+2 more

Serving Winter Park, FL and surrounding areas

Approved

In business since 2010

Free estimates

Credit card accepted

Bob?s painting and coatings has been serving Central Florida since 1993 we are a family owned and operated business. We specialize in exterior House painting, roof coating?s and we also have a full service gutter department featuring seamless custom cut gutters, gutter guards and repairs. Workmanship in customer service is our main priorities we want the job done correct The first time and have a long lasting relationship with our customers for the future.

My jobs
My jobs
My jobs
My jobs
My jobs

+3

1 neighbors recently requested a quote
Recommended by68%of homeowners
Avatar for Tingles Painting, LLC
Tingles Painting, LLC
4.7(
81
)
Exterior Home or Structure - Paint or Stain: LargeExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain: Medium+1 more

Serving Winter Park, FL and surrounding areas

Approved

Super Service Award Winner

In business since 2016

Free estimates

Warranties offered

"I have hired Tingles for a metal sunroom painting and screen replacement as well as exterior house washing. Horas was very prompt in responding and inspection with a very reasonable quote. Raheem did an excellent job with the paint and the whole crew was very punctual with the delivery. Sandra their office manager also did great coordinating the required tasks. Id definetly recommend them."
Exterior Paint Job
Exterior Painting
Response time4 hrs
Response rate95%
1 neighbors recently requested a quote
...
Showing 1-10 of 2266

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.