Service area · Orange County
Painting Contractor in Winter Garden, FL
Winter Garden grew up along Plant Street, and the old groves south of State Road 50 now hold developments like Johns Lake Pointe. OverTop, a painting contractor in Winter Garden, FL, paints houses in both.
How did Winter Garden grow up around Plant Street?
Winter Garden was incorporated in 1908 and grew along Plant Street after the Orange Belt Railroad came through, according to Wikipedia. The citrus that built it was lost twice, in the freezes of 1894 and 1895 and again in the 1980s.
The same article names two historic districts, one downtown and one residential. If you own a building in the downtown historic district, our commercial painting page explains how a job there starts.
Where we work
Neighborhoods and communities in and around Winter Garden
- Downtown and Plant StreetDowntown historic district
- Historic Residential DistrictThe city’s second historic district
- Johns Lake PointeSouth of State Road 50
- Stoneybrook WestSouth of State Road 50
- Stonecrest
- Westfield
- Wintermere Pointe
- Flamingo Crossings
- GrovehurstWinter Garden mailing address, 34787
- Oak Park of Winter GardenWinter Garden mailing address, 34787
- Johns LandingWinter Garden mailing address, 34787
- Lake Hickory NutWinter Garden mailing address, 34787
Neighborhood names from Wikipedia and the Orange County Neighborhood Organization Directory (January 2026).
How new are the homes south of State Road 50?
State Road 50 divides the city, and the land south of it, once groves and farmland, now holds large developments such as Johns Lake Pointe and Stoneybrook West (Wikipedia). Across Winter Garden, 65.3% of homes were built in 2000 or later and the median home dates from 2004, according to the US Census ACS 2020-2024 5-year estimates. The median home value is $476,000.
Is Horizon West part of Winter Garden?
Horizon West is a census-designated place in unincorporated Orange County. It has no post office of its own, so its mail can carry a neighboring city’s name. The City of Winter Garden annexes enclaves by agreement with Orange County, as its August 2024 commission minutes show, so the city line moves over time.
Ocoee sits just east of Winter Garden, and our Ocoee painting page covers its HOA communities.
What we paint in Winter Garden
- Interior PaintingWalls, ceilings and trim, with furniture and floors covered and a daily clean-up.
- Exterior PaintingWe pressure clean, patch and caulk, and cover plants and windows before painting.
- Cabinet RefinishingA new color for the cabinets you have, sprayed off the hinges or painted in place.
- Wood StainingDecks, fences and wood doors, washed, sanded and stained, with decks sealed.
- Garage Door PaintingSpray painting for steel, aluminum, wood and fiberglass garage doors.
- Roof PaintingTile, metal and shingle roofs, washed and repaired before they’re painted.
- Epoxy Floor CoatingsGarage and commercial floors, with cracks repaired and the concrete ground or etched.
- Drywall Installation & RepairPatches, full rooms and new walls, with wall and ceiling textures matched.
- Pressure WashingHouses, driveways, pool decks, roofs and screens, with a soft wash on stucco.
- Carpentry & RestorationTrim, door frames, window sills, decks and fences repaired, then painted to match.
- Soffit & Fascia ReplacementSoffit and fascia in wood, aluminum, vinyl or fiber cement, plus gutter work.
Winter Garden at a glance
Local note
Winter Garden was incorporated in 1908, and its citrus was lost in the freezes of 1894 and 1895 and again in the 1980s.
Local note
Horizon West is a census-designated place in unincorporated Orange County. It has no post office of its own, so its mail can carry a neighboring city’s name.
Source: Wikipedia: Horizon West, Florida
Local note
65.3% of Winter Garden’s homes were built in 2000 or later, and the median home value is $476,000.
Source: US Census ACS 2020-2024 5-year estimates (Census Reporter)
Questions and answers
Questions about painting in Winter Garden
Do you paint homes in Johns Lake Pointe and Stoneybrook West?
Our Winter Garden list includes both, along with Stonecrest, Westfield and Wintermere Pointe; if yours isn’t named, call or text (407) 450-2020.
Does Winter Garden have historic districts?
Yes. Wikipedia names two: the downtown historic district around Plant Street and a historic residential district.
Are Oakland and Windermere part of Winter Garden?
No. Oakland and Windermere are separate towns, and Tildenville is a census-designated place.
Ready when you are
Let’s get your project on the calendar.
Call or text for a free written estimate. Our family-owned crew cleans up at the end of every work day.