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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Montello, WI

116 results

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
77,138
Stock #:
06T4114A
VIN:
1GCRYCEF0KZ299664
Red 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival
Kunes Chevrolet GMC of Elkhorn

Sponsored by Kunes Chevrolet GMC of Elkhorn

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

77,138 mi

Elkhorn, WI
84 mi away
Good Deal

$28,637

Year:
2025
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
Fuel type:
Gasoline
Interior color:
JET BLACK
Transmission:
Automatic
Mileage:
10,812
Stock #:
T864A
VIN:
3GCUKCED9SG297423
RED HOT 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,812 mi

Green Bay, WI
83 mi away
Fair Deal

$48,294

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:
Automatic
Mileage:
92,694
Stock #:
C261287A
VIN:
3GCPYCEKXNG201393
NORTHSKY BLUE METALLIC 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,694 mi

Green Bay, WI
79 mi away
Fair Deal

$30,293

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 $1,111 shipping
Good Deal

$35,587

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
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Home delivery from Louisville, TN
Price includes $1,111 shipping
Fair Deal

$30,587

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Silver
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
81,089
Stock #:
M070-2
VIN:
3GCPYCEK0NG182708

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,089 mi

Clintonville, WI
64 mi away
Good Deal

$29,826

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:
White
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
67,825
Stock #:
G293416
VIN:
3GCPYCEH5KG293416
White 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

67,825 mi

Home delivery from West Palm Beach, FL
Price includes $1,935 shipping
Great Deal

$27,829

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
74,770
Stock #:
PT0150
VIN:
1GCRYCEF5KZ198247
Red 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

74,770 mi

Wausau, WI
81 mi away
Good Deal

$27,287

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,828
Stock #:
02X1151A
VIN:
3GCPYCEF6LG184849
Shadow Gray Metallic 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,828 mi

Delavan, WI
87 mi away
Fair Deal

$27,545

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
77,138
Stock #:
06T4114A
VIN:
1GCRYCEF0KZ299664
Red 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

77,138 mi

Elkhorn, WI
84 mi away
Good Deal

$28,637

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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
50,224
Stock #:
H1977A
VIN:
3GCPYCEL6NG197402

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,224 mi

Wausau, WI
80 mi away
Fair Deal

$36,509

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 $356 shipping
Good Deal

$30,282

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 $332 shipping
Good Deal

$33,832

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
38,144
Stock #:
18109-1
VIN:
3GCUKCED9SG208417

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,144 mi

Clintonville, WI
64 mi away
Fair Deal

$43,614

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
94,925
Stock #:
W0237
VIN:
1GCPYCEL0MZ347549
Black 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

94,925 mi

Whitewater, WI
71 mi away
Good Deal
Manufacturer certified

$30,000

Year:
2026
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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
3,560
Stock #:
P25761
VIN:
3GCPKCEK0TG160125
Summit White 2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,560 mi

Home delivery from Scottsdale, AZ
Price includes $1,756 shipping
Fair Deal

$47,055

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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
21,967
Stock #:
13139
VIN:
3GCPDCEK1RG293303
Black 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,967 mi

Home delivery from Mooresville, IN
Price includes $328 shipping
Great Deal

$39,517

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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,122
Stock #:
406-B598
VIN:
1GCPYCEF5KZ375743
Gray 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,122 mi

Home delivery from Huntington, IN
Price includes $843 shipping
Fair Deal

$32,280

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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
26,322
Stock #:
48208
VIN:
3GCUDCED4PG360459
Gray 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,322 mi

Home delivery from Arlington, TX
Price includes $1,310 shipping
Good Deal

$40,312

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
53,768
Stock #:
PM174391
VIN:
1GCPYCEL0NZ174391
Summit White 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

53,768 mi

Home delivery from Pleasantville, NJ
Price includes $1,504 shipping
Good Deal

$36,744

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
14,797
Stock #:
150127A_1
VIN:
3GCPDCEK5RG150127
Summit White 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,797 mi

Home delivery from Sykesville, MD
Price includes $900 shipping
Fair Deal

$43,694

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:
Automatic
Mileage:
54,995
Stock #:
PTS169870A
VIN:
3GCPYCEF7MG105075
Black 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

54,995 mi

Madison, WI
51 mi away
Fair Deal

$35,299

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:
14,080
Stock #:
26RL211A
VIN:
3GCUDCED3RG316519
Red Hot 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,080 mi

Janesville, WI
75 mi away
Fair Deal

$45,316

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