Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Midland, ON
2,014 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Dark Ash Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,022
- Stock #:
- T25317C
- VIN:
- 3GCPDCEK1RG221310
Price drop
-$1,500
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,022 mi
Coldwater, MI
1 mi away
Great Deal
$38,303
$36,803
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 153,929
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
153,929 mi
Watertown, CT
1 mi away
Fair Deal
$20,199
- 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:
- Silver
- Fuel type:
- Gasoline
- Mileage:
- 83,426
- Stock #:
- 25G047B
- VIN:
- 3GCPYCEF0LG109712
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,426 mi
Karnes City, TX
1 mi away
Good Deal
$29,716
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 62,769
- Stock #:
- 6628725A
- VIN:
- 3GCUDCED8RG264868
Price drop
-$1,340
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,769 mi
Lexington, TN
1 mi away
Great Deal
$38,787
$37,447
- 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:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 119,305
- Stock #:
- 2130415T
- VIN:
- 1GCPYCEL4MZ330415
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
119,305 mi
Rigby, ID
1 mi away
Good Deal
$28,887
- Year:
- 2026
- 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:
- 1,750
- Stock #:
- DTB3865A
- VIN:
- 3GCUKCED2TG207546
Price drop
-$2,109
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,750 mi
Merriam, KS
1 mi away
Great Deal
$49,374
$47,265
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,812
- Stock #:
- A6979A
- VIN:
- 3GCPYCEF1LG177419
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,812 mi
Brattleboro, VT
1 mi away
Good Deal
$31,479
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 55,063
- Stock #:
- Y7269
- VIN:
- 1GCPYCEF3KZ428293
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,063 mi
Fort Madison, IA
1 mi away
Fair Deal
$31,128
- 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:
- 18,064
- Stock #:
- RG314970AP
- VIN:
- 3GCPDCEK4RG314970
Price drop
-$2,153
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
18,064 mi
Las Cruces, NM
1 mi away
Great Deal
$43,339
$41,186
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 9,866
- Stock #:
- H5275
- VIN:
- 3GCUKCED1SG337915
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
9,866 mi
Cadillac, MI
1 mi away
Good Deal
$44,269
- 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:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Tampa, FL
1 mi away
Great Deal
$33,489
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 64,822
- Stock #:
- 214656T
- VIN:
- 1GCPYCEH0MZ214656
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
64,822 mi
Bridgeport, NY
1 mi away
Good Deal
$30,065
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 48,090
- Stock #:
- 26T329C
- VIN:
- 1GCPYCEF1MZ253741
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,090 mi
Melbourne, FL
1 mi away
Fair Deal
$35,754
- 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:
- 23,407
- Stock #:
- 6072H
- VIN:
- 3GCPDCEK7RG229878
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,407 mi
Henderson, NV
1 mi away
Good Deal
$39,978
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,079
- Stock #:
- SG338349A
- VIN:
- 3GCPKCEK5SG338349
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,079 mi
Sanford, FL
1 mi away
Great Deal
$41,633
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 33,830
- Stock #:
- 260629A
- VIN:
- 3GCPKCEK2SG170895
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,830 mi
St Louis, MO
1 mi away
Good Deal
$39,999
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 63,623
- Stock #:
- 51283A
- VIN:
- 3GCPYCEFXKG221125
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,623 mi
Enfield, CT
1 mi away
Good Deal
$30,454
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 34,164
- Stock #:
- 63000A
- VIN:
- 3GCPYCEF8MG114626
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,164 mi
Danville, PA
1 mi away
Good Deal
$35,784
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,206
- Stock #:
- MC44647
- VIN:
- 3GCUDCED5RG380075
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,206 mi
Grapevine, TX
1 mi away
Good Deal
$40,272
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,695
- Stock #:
- 260075A
- VIN:
- 3GCPDCEK3NG524812
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,695 mi
Stephenville, TX
1 mi away
Good Deal
$30,700
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 56,969
- Stock #:
- 3927
- VIN:
- 1GCRYCEF9KZ249670
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Belford, NJ
1 mi away
Fair Deal
$29,673
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,446
- Stock #:
- 268208A
- VIN:
- 3GCPDCEK3RG424618
Price drop
-$1,000
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,446 mi
Daytona Beach, FL
1 mi away
Good Deal
$42,873
$41,872
- 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:
- Dark Ash Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,250
- Stock #:
- 26763A
- VIN:
- 3GCPDCEK9RG149045
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,250 mi
Alexandria, MN
1 mi away
Fair Deal
$39,390
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,726
- Stock #:
- E4122
- VIN:
- 1GCPYCEL2NZ158774
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,726 mi
Everett, WA
1 mi away
Great Deal
$38,586
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