$2,600 /week
~$135,200/year
Average CDL driver pay in Winter Garden, Florida.
Browse 1,318 positions in Winter Garden, FloridaMedian Weekly
$2,050
Top Pay (90th)
$5,000
Pay Range
$300 – $9,500
Sign-On Bonus
$2,041
avg across 400 jobs
Pay Distribution in Winter Garden, Florida
How weekly pay is distributed across current job listings.
Salary by Hiring Type in Winter Garden, Florida
Pay varies significantly between Company Drivers (W2), Owner Operators, and Independent Contractors (1099).
Driver Perks & Benefits in Winter Garden, Florida
Percentage of current job listings offering each benefit.
2% Guaranteed Pay
28% Dedicated Routes
68% Pets Allowed
66% Riders Allowed
87% Take Truck Home
Route Types in Winter Garden, Florida
Breakdown of CDL job types by route distance.
Freight Handling in Winter Garden, Florida
Average freight handling breakdown across 1,318 jobs.
Drop & Hook28%
No-Touch94%
Live Load65%
Driver Load6%
Featured Opportunities in Winter Garden, Florida
Top CDL driver positions from verified carriers and preferred partners.
COYOTE XPRESS LLC
CDL A, OTR - ACCEPTING SAP
$1,800 - $2,500 per week
Class A OTR Company Driver (W2, Solo) Dry Van
$1,800 - $2,500 total weekly pay
7 - 14 expected days out
Gurung Trucking LLC
Over the Road 1099 Refrigerated
$1,300 - $1,700 per week
Class A OTR Contract Driver (1099, Solo) Refrigerated
$1,300 - $1,700 gross total weekly pay
7 - 14 expected days out
Ali Star Inc
Owner Operator Class A CDL-Must have own truck
$8,000 - $14,000 per week
Class A OTR Owner Operator Power Only, Hazmat tanker, Refrigerated, Flatbed trailer and Dry Van
$8,000 - $14,000 gross total weekly pay. Paid weekly
Home at least 2 weekends.
Frequently Asked Questions
The average CDL truck driver in Winter Garden, Florida earns $2,600 per week, or approximately $135,200 per year. The median weekly pay is $2,050, based on 1,318 current job listings.
The top 10% of CDL drivers in Winter Garden, Florida earn $5,000 per week, which works out to roughly $260,000 per year. Weekly pay ranges from $300 to $9,500.
Pay varies significantly by hiring type in Winter Garden, Florida. Average weekly pay by category: Owner Operator at $7,235/week, Independent Contractor (1099) at $2,249/week, Company Driver (W2) at $1,627/week. These figures reflect current job listings and may vary based on experience, routes, and carrier.
Among current featured listings, COYOTE XPRESS LLC is offering a CDL A, OTR - ACCEPTING SAP position paying $1,800–$2,500/week.
Yes — 400 jobs in Winter Garden, Florida currently offer sign-on bonuses, with an average bonus of $2,041.
Based on 1,318 current listings in Winter Garden, Florida: 28% offer dedicated routes, 2% include guaranteed pay, 68% allow pets, 66% allow riders, 87% let you take the truck home. Benefits vary by carrier and position type.
With 1,318 open positions and an average pay of $135,200 per year in Winter Garden, Florida, CDL driving remains a strong career option. Top earners make $260,000 per year, and 400 jobs currently offer sign-on bonuses averaging $2,041. Demand for CDL drivers continues to grow as e-commerce and supply chain needs expand.