This directory lists 10 painting contractors serving Winter Park, FL, a community within the greater Orlando metropolitan area. Whether you need interior work or an exterior repaint, these local contractors are available to help homeowners and property owners find qualified, licensed professionals.
Winter Park's humid subtropical climate brings intense sun, high moisture levels, and frequent afternoon storms throughout the summer months. For exterior painting projects in particular, those conditions mean that thorough surface preparation and the right paint products are essential to achieving a finish that holds up over time.
Browse listings below to compare local options.
Stephens & Company
★ 5.0 (21 reviews)
520 N Orlando Ave STE 205, Winter Park, FL 32789
PaintingMagic Brush House Painting
★ 5.0 (36 reviews)
PaintingOrlando Painting Service
★ 5.0 (23 reviews)
665 Harold Ave Suite B, Winter Park, FL 32789
PaintingFlorida Top Painters
★ 5.0 (9 reviews)
PaintingBausmann Painting
★ 5.0 (28 reviews)
941 W Morse Blvd suite 100, Winter Park, FL 32789
PaintingStecher Painting LLC
★ 5.0 (25 reviews)
79050 US-40 Suite 3, Winter Park, CO 80482
PaintingJW Painting Inc.
★ 4.8 (76 reviews)
PaintingWe Paint Everything
★ 4.7 (15 reviews)
3500 Aloma Ave D42, Winter Park, FL 32792
PaintingThe Plummer Painting Company
★ 4.6 (22 reviews)
660 Jackson Ave, Winter Park, FL 32789
PaintingFive Star Painting of Winter Park
★ 4.3 (12 reviews)
2431 Aloma Ave, Winter Park, FL 32792
Hiring a painting contractor in Winter Park, FL
Hiring a painting contractor in Winter Park, FL covers everything from a single accent wall to a full exterior repaint of stucco, wood, or fiber cement. The directory below lists active painting contractors so you can compare and verify.
Florida UV, humidity, and afternoon storms are brutal on exterior coatings — which is why prep matters more than the brand of paint, and why a low-bid exterior repaint often costs more long-term than the right job done once.
How to verify a painting contractor in Florida
Painting contractors aren't state-certified by DBPR the way roofers, plumbers, electricians, HVAC, and general contractors are. Instead, verify them at the county level: in Orange County through the Orange County Contractor Licensing Division, in Seminole County through the Seminole County Building Division, and in Osceola County through Osceola County Building. Ask for a current local business tax receipt, a Certificate of Insurance (general liability and workers' comp) listing you as certificate holder, and proof they are registered with the appropriate county.
Always insist on a Certificate of Insurance (COI) emailed directly from the agent to you — not a PDF the contractor hands over — and check that workers' compensation is in force. If a painting contractor claims a workers' comp exemption, every worker on your property must be either the exempt officer or an employee of a separately insured subcontractor; if someone is injured on your job without coverage, the liability flows back to you as the property owner.
Why verifying matters in Florida
Florida law (§ 489.127, F.S.) makes it a third-degree felony to contract without a license on a project valued at $5,000 or more, or any size project during a declared state of emergency. Verifying licensure before you sign a contract is the single most important step you can take to protect your home and your deposit. Central Florida's hurricane season runs June 1 through November 30, and unlicensed storm-chasing crews routinely move through Orange, Seminole, and Osceola counties after a major event. Confirming an active state license — and an in-state business address you can actually drive to — keeps you out of that risk pool. Painting attracts the most casual operators of any trade, so confirming insurance and a real business presence — not just a Facebook profile — is the minimum filter.
Questions to ask before you hire
- Are you registered as a painting contractor with the county, and can your insurance agent email me the COI directly?
- What's your prep process — pressure wash, scrape, prime — and is it included or extra?
- What brand and product line are you spraying or rolling, and how many coats?
- For exterior in Florida: are you using an elastomeric or 100% acrylic that handles UV and humidity, and what's the manufacturer warranty?
- Who is the lead painter on the job, and will the same crew be there start to finish?
Frequently asked questions
- How long should an exterior paint job last in Florida?
- A high-quality 100% acrylic exterior with proper prep typically lasts 7–10 years on Florida stucco, 5–8 on wood siding. Elastomeric coatings on stucco can stretch that further. Without proper pressure wash and primer, even premium paint can fail in 2–3 years here.
- Do I really need to pressure wash before exterior paint?
- Yes. Central Florida humidity grows mildew on every exterior surface — painting over it traps the spores under the new film, which fails early as bubbles and dark spots. Pressure wash plus an anti-mildew treatment is non-negotiable for an exterior repaint that lasts.
- Is spray or brush-and-roll better for interior walls?
- Spray is faster and gives a smoother finish on new construction or empty rooms. Brush-and-roll gives a slightly heavier mil thickness per coat and is easier to control around furniture and existing finishes. A good painter chooses based on the room, not on what's faster for them.
- Are there HOA color restrictions I need to worry about in Winter Park?
- Yes — many Winter Park-area neighborhoods, especially newer subdivisions, enforce HOA-approved exterior color palettes that require advance approval before you repaint. A reputable painter will ask whether you've submitted the color to the HOA before they put paint on a wall.