Delivery Driver Jobs in Winterset, IA — Hiring Now

As of May 2026, there are 29 delivery driver openings in Winterset, IA. Local pay ranges from $14 to $151,200/year. Listings are updated daily — benefits start Day 1 for most positions.

Amazon Flex

$18-$25/hr Delivery Driver-Independent Contractor job in Winterset

Winterset, IA

$18 - $25

Postmates

Now Hiring in Winterset:Same-day Delivery Driver | Apply Now

Winterset, IA

$3,200 - $5,400

Shipt

Pharmacy Delivery Driver-Winterset,IA | Hiring

Winterset, IA

$3,472 - $5,824

FedEx Ground

Winterset Full-time Opening:Delivery Driver-Package Handler | Hiring

Winterset, IA

$21 - $26

Domino's Pizza

Winterset Delivery Driver-Pizza Delivery Tips Plus Wages with

Winterset, IA

$14 - $20

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional Courier(Gig

Winterset, IA

$3,500 - $6,000

Local Merchant Delivery Network

Independent Contractor Driver-Early Morning

Winterset, IA

$2,400 - $4,200

Wayfair

Winterset Flexible Job:Delivery Driver-Furniture And Appliance Home

Winterset, IA

$21 - $27

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel-Winterset,IA | Hiring

Winterset, IA

$3,000 - $5,500

Express Logistics

Flexible Gig:Delivery Driver-Full Time Local Routes(Winterset)

Winterset, IA

$19 - $24

Instacart

Winterset Pet Supply Delivery Driver($3.2k-$5.3k/Month) | Hiring

Winterset, IA

$3,190 - $5,280

XPO Logistics

Winterset Delivery Driver-Package Handler Box Truck with $22-$28/hr

Winterset, IA

$22 - $28

Delivery Driver Jobs in Winterset — FAQ

How many delivery driver jobs are open in Winterset, IA?
There are currently 29+ delivery driver positions in Winterset, IA. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winterset?
Delivery Driver pay in Winterset varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winterset require experience?
Many delivery driver positions in Winterset welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winterset?
Browse the 29+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Other Driving Jobs in Winterset

Cdl Driver Jobs in Winterset

9 open positions

Yard Jockey Jobs in Winterset

1 open positions

Warehouse Jobs in Winterset

1 open positions

Last updated: May 13, 2026