Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinamac, IN

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Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
11,451
Stock #:
SS1671A
VIN:
3GCUDCED0RG383871
Red Hot 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Indy Auto Man

Sponsored by Indy Auto Man

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,451 mi

Indianapolis, IN
96 mi away
Fair Deal

$45,162

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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
25,140
Stock #:
P1293
VIN:
3GCPDCEK3RG442178
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,140 mi

Hodgkins, IL
82 mi away
Fair Deal
Manufacturer certified

$40,039

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:
32,267
Stock #:
T289222
VIN:
1GCPYCEF3MZ289222
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,267 mi

Bensenville, IL
92 mi away
Fair Deal

$36,278

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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
93,117
Stock #:
AA568A
VIN:
1GCPYCEK1NZ115843
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

93,117 mi

Fort Wayne, IN
79 mi away
Fair Deal

$28,836

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:
64,213
Stock #:
B7006B
VIN:
1GCRYCEF1KZ343008
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

64,213 mi

Bourbonnais, IL
64 mi away
Fair Deal

$29,996

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:
6-Speed Automatic Overdrive
Mileage:
83,964
Stock #:
C26460A
VIN:
1GCPYCEF2MZ364900
Cherry Red Tintcoat 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$972

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,964 mi

Avon, IN
89 mi away
Great Deal

$28,624

$27,914

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:
Black
Transmission:
Automatic
Mileage:
108,735
Stock #:
PM31343
VIN:
1GCPYCEF5LZ274946
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,170

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,735 mi

Kokomo, IN
48 mi away
Great Deal

$26,702

$24,532

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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
86,984
Stock #:
YP716
VIN:
1GCPYCEH4KZ399582
Red Hot 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$2,762

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

86,984 mi

Danville, IL
78 mi away
Great Deal

$28,607

$25,845

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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
30,716
Stock #:
CC2036
VIN:
3GCPDCEK8RG179394
Glacier Blue Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,716 mi

Avon, IN
89 mi away
Fair Deal

$38,606

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Slate Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
52,778
Stock #:
B19182A
VIN:
3GCUDCE8XRG358530
Slate Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,778 mi

Anderson, IN
84 mi away
Great Deal

$36,490

Year:
2023
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
35,093
Stock #:
HCVPPG361993
VIN:
3GCUDCED7PG361993
Summit White 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$800

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,093 mi

Noblesville, IN
77 mi away
Great Deal

$39,010

$38,210

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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
80,389
Stock #:
103642
VIN:
3GCPDCEK6RG103642
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,389 mi

Home delivery from Mobile, AL
Price includes $1,446 shipping
Fair Deal

$35,641

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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
25,140
Stock #:
P1293
VIN:
3GCPDCEK3RG442178
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,140 mi

Hodgkins, IL
82 mi away
Fair Deal
Manufacturer certified

$40,039

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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
52,070
Stock #:
70109A
VIN:
3GCPDCEK8PG284157
Glacier Blue Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,070 mi

Frankfort, IL
71 mi away
Fair Deal
Manufacturer certified

$36,618

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:
SAND DUNE METALLIC
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
98,341
Stock #:
DN680533
VIN:
3GCPDCED9NG680533
SAND DUNE METALLIC 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,341 mi

Home delivery from Houston, TX
Price includes $834 shipping
Fair Deal

$31,629

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:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,775
Stock #:
5019
VIN:
1GCPYCEF0LZ168095
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,775 mi

Home delivery from Burton, MI
Price includes $203 shipping
Great Deal

$29,103

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:
Blue
Fuel type:
Gasoline
Interior color:
Black (Charcoal)
Transmission:
6-Speed Automatic
Mileage:
86,215
Stock #:
7249
VIN:
1GCPYCEF7LZ285754

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

86,215 mi

La Porte, IN
41 mi away
Fair Deal

$29,699

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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,524
Stock #:
C4914A
VIN:
3GCPYCEF6MG480715
Summit White 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,524 mi

Morris, IL
94 mi away
Good Deal
Manufacturer certified

$31,376

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:
51,002
Stock #:
26582A
VIN:
1GCPYCEF3MZ403056
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,002 mi

Peotone, IL
63 mi away
Fair Deal

$34,413

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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
79,997
Stock #:
256943
VIN:
1GCPYCEF6MZ256943
Blue 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$3,900

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,997 mi

Home delivery from Monroe, LA
Price includes $662 shipping
Good Deal

$34,952

$31,052

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:
CYPRESS GRAY
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
JET BLACK
Transmission:
Automatic
Mileage:
11,352
Stock #:
277668A
VIN:
3GCPKCEK7SG347277
CYPRESS GRAY 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,352 mi

Home delivery from Madison, WI
Price includes $195 shipping
Fair Deal

$44,422

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:
84,249
Stock #:
GM31867T
VIN:
1GCPYCEF6MZ370442
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,249 mi

Home delivery from Gurnee, IL
Price includes $224 shipping
Great Deal

$27,100

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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
52,070
Stock #:
70109A
VIN:
3GCPDCEK8PG284157
Glacier Blue Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,070 mi

Frankfort, IL
71 mi away
Fair Deal
Manufacturer certified

$36,618

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winamac, IN?

The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,418.75. The average price has decreased by -2.5% since last year. The 183 for sale near Winamac, IN on CarGurus, range from $21,300 to $64,722 in price.

How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winamac, IN have no reported accidents or damage?

176 out of 183 for sale near Winamac, IN have no reported accidents or damage.

What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?

Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG/MPGe.

What fuel types are available?

Diesel, Flex Fuel Vehicle, Gasoline engines are available.

*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.

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