CarGurus Header
Location:

Include delivery listings?

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Le Roy, IL

165 results

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
6,937
Stock #:
PL2977A
VIN:
3GCPKCEK4SG177072
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Lexus of Peoria

Sponsored by Lexus of Peoria

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,937 mi

Peoria, IL
54 mi away
Good Deal

$42,566

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Ash
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
47,504
Stock #:
4589H
VIN:
3GCPDCEK0PG173098
Ash 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,504 mi

Pekin, IL
49 mi away
Good Deal

$36,619

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
60,411
Stock #:
QBP6561
VIN:
3GCPYCEF3MG349855
Black 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$1,000

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,411 mi

Bloomington, IL
13 mi away
Good Deal

$33,819

$32,819

Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,339
Stock #:
MX4446
VIN:
1GCPYCEL1MZ352307
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Home delivery from Louisville, TN
Price includes $725 shipping
Good Deal

$35,201

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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,839
Stock #:
MX4469
VIN:
1GCPYCEF2LZ149662
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Home delivery from Louisville, TN
Price includes $725 shipping
Fair Deal

$30,201

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Ash
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
47,504
Stock #:
4589H
VIN:
3GCPDCEK0PG173098
Ash 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,504 mi

Pekin, IL
49 mi away
Good Deal

$36,619

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:
Silver ICE Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
JET BLACK, CLOTH SEAT TRIM
Transmission:
Automatic
Mileage:
59,213
Stock #:
C548903
VIN:
1GCPYCEF0MZ429663
Silver ICE Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,082

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,213 mi

Mendota, IL
84 mi away
Good Deal

$35,821

$34,739

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
28,679
Stock #:
5AT-010
VIN:
3GCPDCEK7PG202581
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,679 mi

Home delivery from Mount Orab, OH
Price includes $884 shipping
Great Deal

$37,634

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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,169
Stock #:
210868
VIN:
1GCPYCEFXLZ210868
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,169 mi

Morton, IL
41 mi away
Good Deal

$34,404

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
6,937
Stock #:
PL2977A
VIN:
3GCPKCEK4SG177072
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,937 mi

Peoria, IL
54 mi away
Good Deal

$42,566

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:
Blue
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
72,552
Stock #:
C39198
VIN:
3GCPYCEFXKG234862
Blue 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$801

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,552 mi

Home delivery from Cincinnati, OH
Price includes $478 shipping
Good Deal

$31,665

$30,864

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:
Blue
Fuel type:
Gasoline
Transmission:
6-Speed Automatic
Mileage:
46,199
Stock #:
232880
VIN:
1GCPYCEF5MZ234836
Blue 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,199 mi

Terre Haute, IN
94 mi away
Fair Deal

$35,223

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
60,411
Stock #:
QBP6561
VIN:
3GCPYCEF3MG349855
Black 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$1,000

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,411 mi

Bloomington, IL
13 mi away
Good Deal

$33,819

$32,819

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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
117,765
Stock #:
SG1791
VIN:
1GCPYCEF8KZ351436
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

117,765 mi

Champaign, IL
31 mi away
Fair Deal

$26,814

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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
116,709
Stock #:
D11212
VIN:
3GCPYCEFXKG115726
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,709 mi

Home delivery from Mt Juliet, TN
Price includes $470 shipping
Great Deal

$23,858

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:
Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
46,234
Stock #:
S2025A
VIN:
1GCPYCEFXMZ401479
Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,234 mi

Palmyra, IL
91 mi away
Fair Deal

$36,338

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
77,725
Stock #:
P13746A
VIN:
3GCPDCEK4PG170463
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,725 mi

Home delivery from Roswell, GA
Price includes $1,000 shipping
Good Deal

$34,740

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
71,526
Stock #:
53595
VIN:
1GCPYCEK6NZ234598
Northsky Blue Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,526 mi

Home delivery from Cambridge, OH
Price includes $284 shipping
Great Deal

$30,210

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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
50,884
Stock #:
244226
VIN:
1GCPYCEF6MZ244226
Cherry Red Tintcoat 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,884 mi

Home delivery from Washington, MI
Price includes $343 shipping
Good Deal

$33,843

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
103,439
Stock #:
1926938
VIN:
1GCRYCEF9KZ226938

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

103,439 mi

Peoria, IL
54 mi away
Good Deal

$24,402

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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
171,876
Stock #:
A530A
VIN:
1GCPYCEFXLZ104226
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$500

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

171,876 mi

Dwight, IL
54 mi away
Good Deal

$20,865

$20,365

Year:
2022
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
115,268
Stock #:
K165409A
VIN:
3GCPDCED7NG675427
Black 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,268 mi

Peoria, IL
54 mi away
Good Deal

$27,375

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
20,075
Stock #:
260201A
VIN:
3GCPDCEK6RG209699
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,075 mi

Joliet, IL
87 mi away
Good Deal

$40,220

Page 1 of 8

A better way to discover your best deal

Let us help you find a car you’ll love.

CarGurus Footer