Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWindsor, VT
157 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 68,630
- Stock #:
- 110992
- VIN:
- 3GCPDCEK0NG534178
Price drop
-$1,400
Sponsored by CarFive Plaistow
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,630 mi
Plaistow, NH
81 mi away
Good Deal
$33,195
$31,795
- 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:
- Automatic
- Mileage:
- 73,718
- Stock #:
- 47682C
- VIN:
- 1GCRYCEF8KZ178395
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
73,718 mi
St Albans, VT
99 mi away
Great Deal
$25,087
- 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:
- 82,743
- Stock #:
- MK3086
- VIN:
- 1GCPYCEF1MZ371756
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,743 mi
Epsom, NH
57 mi away
Fair Deal
$30,698
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 82,401
- Stock #:
- T262186A
- VIN:
- 3GCPYCEF5LG403610
Price drop
-$1,882
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,401 mi
Ballston Spa, NY
77 mi away
Good Deal
$29,027
$27,145
- 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:
- 79,568
- Stock #:
- U1200390B
- VIN:
- 1GCPYCEFXMZ315251
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,568 mi
Tilton, NH
44 mi away
Fair Deal
$31,985
- 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:
- 91,842
- Stock #:
- 43999
- VIN:
- 3GCPYCEF3MG435456
Price drop
-$1,000
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,842 mi
Albany, NY
86 mi away
Good Deal
$30,000
$29,000
- 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:
- 97,152
- Stock #:
- G22238A
- VIN:
- 1GCPYCEF6KZ406692
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
97,152 mi
Rochester, NH
74 mi away
Great Deal
$24,698
- 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:
- 51,489
- Stock #:
- T58111
- VIN:
- 3GCPDCEK1PG158111
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,489 mi
Concord, NH
52 mi away
Good Deal
$34,183
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 16,847
- Stock #:
- 101543C
- VIN:
- 1GCPYCEK7NZ101543
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
16,847 mi
Framingham, MA
97 mi away
Great Deal
$34,995
- 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
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,887
- Stock #:
- 260706B
- VIN:
- 3GCPDCEKXRG256007
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,887 mi
Claremont, NH
11 mi away
Fair Deal
$39,432
- 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:
- 23,379
- Stock #:
- 5800
- VIN:
- 3GCUKCED6SG177255
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,379 mi
Fitchburg, MA
71 mi away
Good Deal
$42,999
- 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:
- White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 129,579
- Stock #:
- 296447-A
- VIN:
- 1GCPYCEF0KZ296447
Price drop
-$1,899
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
129,579 mi
Peabody, MA
99 mi away
Great Deal
$21,180
$19,980
- 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:
- 68,630
- Stock #:
- 110992
- VIN:
- 3GCPDCEK0NG534178
Price drop
-$1,400
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,630 mi
Plaistow, NH
81 mi away
Good Deal
$33,195
$31,795
- 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 Hot
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 64,008
- Stock #:
- R10057A
- VIN:
- 3GCPYCEF5MG139791
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
64,008 mi
Rochester, NH
74 mi away
Fair Deal
$33,694
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,903
- Stock #:
- 610597T
- VIN:
- 3GCPDCED4NG610597
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Gorham, NH
91 mi away
Good Deal
$35,689
- 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
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 37,036
- Stock #:
- E14067A
- VIN:
- 3GCPDCEK1RG305546
Price drop
-$1,622
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
37,036 mi
Newport, NH
16 mi away
Good Deal
$39,293
$37,671
- 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:
- 89,338
- Stock #:
- E14395A
- VIN:
- 3GCPDCED9NG583834
Price drop
-$1,004
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,338 mi
Newport, NH
16 mi away
Fair Deal
$32,797
$31,793
- 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:
- 72,492
- Stock #:
- G261063A
- VIN:
- 3GCPYCEF0KG120479
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
72,492 mi
Nashua, NH
73 mi away
Fair Deal
$29,437
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,596
- Stock #:
- 23082A
- VIN:
- 1GCPYCEL8MZ386485
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,596 mi
Montpelier, VT
53 mi away
Good Deal
$34,487
- 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:
- 112,301
- Stock #:
- 2512B
- VIN:
- 3GCPYCEF6LG326620
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,301 mi
Ludlow, VT
14 mi away
Fair Deal
$25,995
- 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:
- 22,826
- Stock #:
- N2200549A
- VIN:
- 3GCPDCEK4PG281501
Price drop
-$1,012
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,826 mi
Lowell, MA
84 mi away
Good Deal
$40,018
$39,006
- 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:
- 93,690
- Stock #:
- 26M874A
- VIN:
- 3GCPYCEF7LG236263
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,690 mi
Manchester, NH
63 mi away
Fair Deal
$29,540
- Year:
- 2020
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 76,626
- Stock #:
- 44518
- VIN:
- 1GCPYCEH0LZ316876
Price drop
-$1,600
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,626 mi
Albany, NY
86 mi away
Good Deal
$29,100
$27,500
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,596
- Stock #:
- 23082A
- VIN:
- 1GCPYCEL8MZ386485
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,596 mi
Montpelier, VT
53 mi away
Good Deal
$34,487
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Windsor, VT?
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 116 for sale near Windsor, VT on CarGurus, range from $20,180 to $66,097 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Windsor, VT have no reported accidents or damage?
101 out of 116 for sale near Windsor, VT 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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