Driving Jobs in Winter Garden, FL — Apply Today

As of October 2026, there are 20+ open driving jobs in Winter Garden, FL. Current pay ranges from $32 to $382,200 per year. Top hiring areas include Delivery Driver, Cdl A and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Nightline Freight

Part-Time Overnight Parcel Transfer Driver – Winter Garden

Winter Garden, FL

$3,276 - $4,732

Peak Season Logistics

Part-Time Role in Winter Garden:Seasonal Holiday Package Driver

Winter Garden, FL

$4,024 - $5,750

Metro Parcel Delivery

Winter Garden Part-Time:Urban Step Van Courier(Hiring) | Part

Winter Garden, FL

$4,180 - $6,050

Health Transit Logistics

Part-Time Job in Winter Garden:Medical & Pharmacy Package Courier

Winter Garden, FL

$2,720 - $3,825

Flex Delivery Network

Part-Time Independent Parcel Courier – Winter Garden FL | Part

Winter Garden, FL

$2,000 - $4,000

Weekend Transit Co.

Student-Friendly Part-Time Weekend Parcel Delivery Driver in

Winter Garden, FL

$1,365 - $2,275

Heavy Haul Last Mile

Winter Garden Part-Time:Heavy/bulky Item Delivery Specialist

Winter Garden, FL

$3,458 - $5,005

Corporate Courier Logistics

Part-Time B2B Route Logistics Driver|Winter Garden,FL | Part Time

Winter Garden, FL

$2,720 - $4,080

E-Comm Transit Solutions

Part-Time E-commerce Delivery Specialist(Winter Garden,FL)|E-comm

Winter Garden, FL

$3,360 - $5,040

Local Logistics Pros

Winter Garden Part-Time Job:Local Package Delivery Driver | Part

Winter Garden, FL

$3,360 - $5,040

Schneider National

CDL A Truck Driver - OTR Dry Van

Winter Garden, FL

$71,250 - $91,200

Crete Carrier

CDL A Truck Driver - Regional Dry Van Home Weekly

Winter Garden, FL

$68,400 - $87,400

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 20+ open driving jobs in Winter Garden, FL. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Winter Garden?
Pay in Winter Garden depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Winter Garden with no experience?
Yes. Many employers in Winter Garden run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Winter Garden that is home every night?
Local routes in Winter Garden are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Winter Garden?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Winter Garden?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Winter Garden?
Many carriers, delivery firms and local fleets in Winter Garden hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 20+ open routes above and apply directly.

Last updated: October 05, 2026