CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Newburgh, IN

180 results
Newburgh, IN
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Gary Mathews Motors Incorporated

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,745 miles

$32,000

Fair Deal
Clarksville, TN
99 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,745
Stock number:
L13183
VIN:
1GCPYCEF7MZ266235

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,365 miles

$26,376

Fair Deal
Benton, KY
91 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
98,365
Stock number:
A99945
VIN:
3GCPYCEH0KG199945

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

137,393 miles

$19,999

Great Deal
Bedford, IN
77 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
137,393
Stock number:
FP565A
VIN:
1GCPYCEF2KZ352064

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,663 miles

$31,995

Fair Deal
Paducah, KY
91 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cajun Red Tintcoat
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
68,663
Stock number:
G26225A
VIN:
1GCPYCEF7LZ306182

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

137,393 miles

$19,999

Great Deal
Bedford, IN
77 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
137,393
Stock number:
FP565A
VIN:
1GCPYCEF2KZ352064

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,745 miles

$32,000

Fair Deal
Clarksville, TN
99 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,745
Stock number:
L13183
VIN:
1GCPYCEF7MZ266235

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,443 miles

$29,990

Good Deal
Evansville, IN
5 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
78,443
Stock number:
MG101814D
VIN:
3GCPYCEFXMG101814

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,657 miles

$32,999

Fair Deal
Bloomington, IN
95 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
54,657
Stock number:
368823A
VIN:
1GCPYCEF5LZ127851

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,348 miles

$34,295

Good Deal
Salem, IN
85 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Sand Dune Metallic
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,348
Stock number:
S11001T-1
VIN:
3GCUDCET9NG555963

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,598 miles

$29,624

Great Deal
Louisville, KY
87 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Red
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
44,598
Stock number:
34T3887A
VIN:
3GCPYCEK7NG194225

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,598 miles

$29,624

Great Deal
Louisville, KY
87 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Red
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
44,598
Stock number:
34T3887A
VIN:
3GCPYCEK7NG194225

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Indiana
  6. / Newburgh
  • Chevrolet Silverado 1500 LT in Newburgh IN

  • Chevrolet Silverado 1500 RST in Newburgh IN

  • Chevrolet Silverado 1500 LTZ in Newburgh IN

  • Chevrolet Silverado 1500 LT Trail Boss in Newburgh IN

  • Chevrolet Silverado 1500 LT1 in Newburgh IN

  • Chevrolet Silverado 1500 High Country in Newburgh IN

  • Chevrolet Silverado 1500 Custom in Newburgh IN

  • Chevrolet Silverado 1500 Custom Trail Boss in Newburgh IN

  • Chevrolet Silverado 1500 Work Truck in Newburgh IN

  • Chevrolet Silverado 1500 in Evansville IN

  • Chevrolet Silverado 1500 in Owensboro KY

  • Chevrolet Silverado 1500 in Jasper IN

  • Chevrolet Silverado 1500 in Bowling Green KY

  • Chevrolet Silverado 1500 in Paducah KY

  • Chevrolet Silverado 1500 in Louisville KY

  • Chevrolet Silverado 1500 in Bloomington IN

  • Chevrolet Silverado 1500 in Clarksville TN

  • Chevrolet Silverado 1500 in Carbondale IL

  • Chevrolet Silverado 1500 in Newburgh IN

  • Old Chevy Trucks for Sale in Newburgh IN

  • Classic Muscle Cars for Sale in Newburgh IN

  • Chevrolet Trucks For Sale in Newburgh IN

  • Cheap Muscle Cars for Sale in Newburgh IN

  • Work Trucks for Sale in Newburgh IN

  • Reliable Cars For Sale in Newburgh IN

  • American Made Trucks For Sale in Newburgh IN

  • Best Pickup Trucks For Sale in Newburgh IN

  • Best Cars Under $5,000 For Sale in Newburgh IN

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Newburgh IN

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Steve Faulkner Chevrolet Buick GMC

  • Law Chevrolet Buick

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.