CarGurus Header
Location:

Include delivery listings?

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

78 results

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 $1,508 shipping
Good Deal

$35,984

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

$42,694

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 $2,268 shipping
Great Deal

$28,162

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

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,199 mi

Home delivery from Terre Haute, IN
Price includes $548 shipping
Fair Deal

$35,771

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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
75,873
Stock #:
613201
VIN:
3GCPYCEF7LG357312
Summit White 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

75,873 mi

Home delivery from Pine City, MN
Price includes $270 shipping
Good Deal

$30,120

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:
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 $1,508 shipping
Fair Deal

$30,984

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 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

62,775 mi

Home delivery from Burton, MI
Price includes $435 shipping
Great Deal

$29,785

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Red
Fuel type:
Diesel
Interior color:
Black
Mileage:
110,590
Stock #:
301317
VIN:
3GCUDCE84PG301317
Red 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,590 mi

Home delivery from Euless, TX
Price includes $1,552 shipping
Fair Deal

$31,548

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 $1,563 shipping
Good Deal

$40,565

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 $477 shipping
Good Deal

$33,977

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 $1,760 shipping
Fair Deal

$37,000

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
10-Speed Automatic
Mileage:
16,913
Stock #:
R87954
VIN:
3GCUKCED9SG358155
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 10-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,913 mi

Home delivery from Herculaneum, MO
Price includes $1,200 shipping
Fair Deal

$47,818

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:
Mosaic Black Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,771
Stock #:
5048
VIN:
1GCPYCEL5NZ100710
Mosaic Black Metallic 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

54,771 mi

Home delivery from Seffner, FL
Price includes $1,452 shipping
Good Deal

$34,936

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

Home delivery from Wausau, WI
Price includes $142 shipping
Good Deal

$27,429

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
85,115
Stock #:
26168
VIN:
1GCPYCEK8NZ134843
Summit White 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,115 mi

Home delivery from Shawnee, KS
Price includes $882 shipping
Fair Deal

$31,370

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
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
100,334
Stock #:
42380
VIN:
1GCPYCEF8MZ317516
Black 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,334 mi

Home delivery from Springfield, IL
Price includes $498 shipping
Fair Deal

$30,371

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:
Brown Metallic
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
78,081
Stock #:
T00272
VIN:
1GCPYCEH2KZ217314
Brown Metallic 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

78,081 mi

Home delivery from Hermitage, PA
Price includes $639 shipping
Fair Deal

$30,128

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 $1,816 shipping
Fair Deal

$46,415

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:
Red
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
104,499
Stock #:
14237
VIN:
1GCPYCEF8MZ381894
Red 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

104,499 mi

Home delivery from Rogers, MN
Price includes $378 shipping
Fair Deal

$29,627

Year:
2021
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
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
51,860
Stock #:
G478752
VIN:
3GCPYCEH0MG478752
Red 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

51,860 mi

Home delivery from Houston, TX
Price includes $1,832 shipping
Good Deal

$34,054

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
61,142
Stock #:
6-1339
VIN:
3GCUDCED2RG163437
Summit White 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,142 mi

Home delivery from Mesa, AZ
Price includes $1,818 shipping
Fair Deal

$41,416

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:
Red
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
155,893
Stock #:
14093
VIN:
1GCPYCEF8MZ147433
Red 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

155,893 mi

Home delivery from Rogers, MN
Price includes $378 shipping
Fair Deal

$23,627

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:
Sand Dune Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
70,248
Stock #:
6D535A-1
VIN:
3GCPDCEK9NG685360
Vehicle photo unavailable

Preparing for a close up...

Photos coming soon

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,248 mi

Home delivery from Altoona, PA
Price includes $1,128 shipping
Fair Deal

$33,590

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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,388
Stock #:
313046
VIN:
3GCUDCED8PG313046
Dark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,388 mi

Home delivery from Euless, TX
Price includes $1,863 shipping
Fair Deal

$37,534

Page 1 of 4

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Bayfield, WI?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,275.24. The average price has decreased by -1.8% since last year. The 76 for sale near Bayfield, WI on CarGurus, range from $22,128 to $65,811 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Bayfield, WI have no reported accidents or damage?
66 out of 76 for sale near Bayfield, WI 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.

A better way to discover your best deal

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

CarGurus Footer