Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPoughkeepsie, NY
186 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 154,125
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
Sponsored by Shaker Family Ford Lincoln
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
154,125 mi
Watertown, CT
43 mi away
Fair Deal
$20,099
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,506
- Stock #:
- P1822
- VIN:
- 3GCPKCEK0SG333141
New arrival
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,506 mi
Brodheadsville, PA
95 mi away
Fair Deal
$45,314
- 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
- Transmission:
- Automatic
- Mileage:
- 76,152
- Stock #:
- SS26442
- VIN:
- 1GCPYCEK1NZ122887
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,152 mi
Lake Katrine, NY
18 mi away
Fair Deal
$32,594
- 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:
- 154,125
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
154,125 mi
Watertown, CT
43 mi away
Fair Deal
$20,099
- 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
89 mi away
Fair Deal
$29,673
- 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:
- 61,817
- Stock #:
- J1954A
- VIN:
- 1GCPYCEF5KZ412192
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
61,817 mi
Old Saybrook, CT
84 mi away
Fair Deal
$30,869
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,506
- Stock #:
- P1822
- VIN:
- 3GCPKCEK0SG333141
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,506 mi
Brodheadsville, PA
95 mi away
Fair Deal
$45,314
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 64,109
- Stock #:
- 8689
- VIN:
- 1GCRYCEF5KZ313123
Price drop
-$2,000
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
64,109 mi
Willimantic, CT
89 mi away
Fair Deal
$31,684
$29,684
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 4,286
- Stock #:
- PM213863
- VIN:
- 3GCUKCE89SG213863
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,286 mi
Honesdale, PA
69 mi away
Great Deal
$43,945
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 29,769
- Stock #:
- T52696B
- VIN:
- 3GCUDCE87RG153960
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,769 mi
Pittsfield, MA
62 mi away
Great Deal
$39,518
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 40,742
- Stock #:
- 56866T
- VIN:
- 1GCPYCEF8MZ245765
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
40,742 mi
Bay Shore, NY
75 mi away
Fair Deal
$36,495
- 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
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 102,783
- Stock #:
- 5211
- VIN:
- 3GCPYCEF9MG436837
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
102,783 mi
Old Saybrook, CT
84 mi away
Good Deal
$28,043
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 73,499
- Stock #:
- P20921A
- VIN:
- 1GCRYCEH8LZ331635
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
73,499 mi
Pittston, PA
99 mi away
Fair Deal
$28,844
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 28,853
- Stock #:
- 56894T
- VIN:
- 3GCUDCED4RG384439
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,853 mi
Bay Shore, NY
75 mi away
Fair Deal
$42,950
- 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:
- 34,003
- Stock #:
- PV26086A
- VIN:
- 3GCPDCEKXRG398597
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,003 mi
Chicopee, MA
76 mi away
Fair Deal
$42,663
- 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:
- 104,108
- Stock #:
- 332395C01
- VIN:
- 1GCPYCEF2KZ332395
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,108 mi
Linden , NJ
77 mi away
Good Deal
$24,799
- 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:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 57,412
- Stock #:
- CT12064
- VIN:
- 1GCRYCEF4KZ223400
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,412 mi
Manchester, CT
70 mi away
Good Deal
$28,294
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 9,197
- Stock #:
- SG359909
- VIN:
- 3GCUKCED6SG359909
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
9,197 mi
Home delivery from Forney, TX
Price includes $2,070 shipping
Fair Deal
$48,216
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 7,734
- Stock #:
- 261810B
- VIN:
- 3GCUKCED6SG297251
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,734 mi
Mahwah, NJ
44 mi away
Fair Deal
$47,898
- 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
- Transmission:
- Automatic
- Mileage:
- 109,668
- Stock #:
- 26718BB
- VIN:
- 1GCPYCEF5MZ449682
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
109,668 mi
Lake Katrine, NY
18 mi away
Great Deal
$26,174
- 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:
- 43,307
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
31 mi away
Good Deal
$37,986
- 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:
- 62,213
- Stock #:
- N6865A
- VIN:
- 1GCPYCEF4MZ321580
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,213 mi
Cheshire, CT
54 mi away
Good Deal
$32,774
- 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:
- 82,389
- Stock #:
- T262186A
- VIN:
- 3GCPYCEF5LG403610
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,389 mi
Ballston Spa, NY
88 mi away
Fair Deal
$30,175
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 7,248
- Stock #:
- C45735
- VIN:
- 3GCPKCEK9SG145735
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,248 mi
Mt Pocono, PA
86 mi away
Good Deal
$43,959
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Poughkeepsie, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,855.08. The average price has decreased by -0.7% since last year. The 144 for sale near Poughkeepsie, NY on CarGurus, range from $20,099 to $65,675 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Poughkeepsie, NY have no reported accidents or damage?
127 out of 144 for sale near Poughkeepsie, NY 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 23 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
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