Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearFishkill, NY
181 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:
- 355 hp 5.3L V8
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 40,116
- Stock #:
- 5058A
- VIN:
- 3GCPDCED9NG690981
Price drop
-$3,282
Sponsored by Hawthorne Chevrolet
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
40,116 mi
Hawthorne, NJ
41 mi away
Good Deal
$41,230
$37,948
- 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
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,769 mi
Pittsfield, MA
72 mi away
Great Deal
$39,404
- 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
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
26 mi away
Good Deal
$38,369
- 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
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,286 mi
Honesdale, PA
70 mi away
Great Deal
$44,385
- 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:
- Sand Dune Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 87,472
- Stock #:
- F26133A
- VIN:
- 3GCPDCED5NG679251
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
87,472 mi
Bethlehem, PA
99 mi away
Fair Deal
$34,191
- 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
77 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:
- 153,929
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
153,929 mi
Watertown, CT
41 mi away
Fair Deal
$20,287
- 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:
- 88,583
- Stock #:
- 43952
- VIN:
- 1GCPYCEK0NZ156612
Price drop
-$1,500
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,583 mi
Albany, NY
82 mi away
Good Deal
$30,175
$28,675
- 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
72 mi away
Great Deal
$39,404
- 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:
- Automatic
- Mileage:
- 25,595
- Stock #:
- GB0401
- VIN:
- 3GCPDCEK8PG340310
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
15 mi away
Good Deal
$37,566
- 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
Home delivery from Tampa, FL
Price includes $1,101 shipping
Good Deal
$36,080
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,063
- Stock #:
- N12692A
- VIN:
- 3GCPKCEK5SG103787
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
45,063 mi
Washington, NJ
79 mi away
Great Deal
$37,540
- 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
Price drop
-$1,000
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,108 mi
Linden , NJ
66 mi away
Good Deal
$25,799
$24,799
- 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
80 mi away
Fair Deal
$28,543
- 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
Price drop
-$900
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $472 shipping
Good Deal
$37,161
$36,261
- 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:
- Automatic
- Mileage:
- 125,117
- Stock #:
- CU378338
- VIN:
- 1GCPYCEF0KZ378338
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,117 mi
Middletown, CT
64 mi away
Fair Deal
$24,492
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 156,112
- Stock #:
- 310350-1
- VIN:
- 3GCPYCEF2KG310350
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
156,112 mi
Albany, NY
80 mi away
Good Deal
$20,163
- 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:
- 53,803
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,803 mi
Home delivery from Pleasantville, NJ
Price includes $212 shipping
Good Deal
$35,447
- 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
71 mi away
Good Deal
$28,494
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $701 shipping
Great Deal
$32,611
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $312 shipping
Fair Deal
$31,589
- 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:
- Blue
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 63,156
- Stock #:
- 202263156
- VIN:
- 3GCPDCED0NG574584
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,156 mi
Scranton, PA
93 mi away
Good Deal
$34,995
- 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:
- 43,490
- Stock #:
- 313824
- VIN:
- 1GCRYCEF2KZ313824
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
43,490 mi
Huntington Sta, NY
55 mi away
Fair Deal
$33,065
- 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:
- Automatic
- Mileage:
- 91,959
- Stock #:
- KM26244
- VIN:
- 1GCPYCEF3LZ194321
Price drop
-$600
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,959 mi
Lake Katrine, NY
30 mi away
Good Deal
$27,674
$27,074
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Fishkill, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,080.70. The average price has decreased by -0.4% since last year. The 146 for sale near Fishkill, NY on CarGurus, range from $20,287 to $64,757 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Fishkill, NY have no reported accidents or damage?
146 out of 146 for sale near Fishkill, 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 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
Relevant articles
Craig Fitzgerald
The Best Trucks Under $25,000 in 2026
New trucks cost more than ever, but the prices of used ones finally seem to be cooling. You still can't find the latest and fanciest full-sizes for budget prices, but fortunately, there are plenty of good trucks under $25,000 these days. Here, we've assembled a list of the best.
Craig Fitzgerald
The Best Cars to Tow Behind an RV in 2026
Not many new models can be towed behind an RV. We’ve identified several that are recommended for flat-towing according to their owner’s manual, and a few used models that have fewer technological or engineering restrictions.
CarGurus Editorial Team
Car Deals with 0% APR in July 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
Chevrolet Silverado 1500 LT in Fishkill NYChevrolet Silverado 1500 RST in Fishkill NYChevrolet Silverado 1500 LTZ in Fishkill NYChevrolet Silverado 1500 LT Trail Boss in Fishkill NYChevrolet Silverado 1500 LT1 in Fishkill NYChevrolet Silverado 1500 Custom in Fishkill NYChevrolet Silverado 1500 High Country in Fishkill NYChevrolet Silverado 1500 Custom Trail Boss in Fishkill NYChevrolet Silverado 1500 Work Truck in Fishkill NY
Chevrolet Silverado 1500 in Newburgh NYChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in New Haven CTChevrolet Silverado 1500 in New York NYChevrolet Silverado 1500 in Hartford CTChevrolet Silverado 1500 in Holtsville NYChevrolet Silverado 1500 in Pittsfield MAChevrolet Silverado 1500 in Albany NYChevrolet Silverado 1500 in New Brunswick NJ
Chevrolet Silverado 1500 in Fishkill NYOld Chevy Trucks for Sale in Fishkill NYClassic Muscle Cars for Sale in Fishkill NYChevrolet Trucks For Sale in Fishkill NYCheap Muscle Cars for Sale in Fishkill NYWork Trucks for Sale in Fishkill NYReliable Cars For Sale in Fishkill NYAmerican Made Trucks For Sale in Fishkill NYBest Pickup Trucks For Sale in Fishkill NYBest Cars Under $5,000 For Sale in Fishkill NY
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in FishkillUsed SUVs / Crossovers for Sale with Low Mileage in FishkillUsed Hatchbacks for Sale with Low Mileage in FishkillUsed Convertibles for Sale with Low Mileage in FishkillUsed Vans for Sale with Low Mileage in FishkillUsed Minivans for Sale with Low Mileage in FishkillUsed Pickup Trucks for Sale with Low Mileage in FishkillUsed Coupes for Sale with Low Mileage in FishkillUsed Wagons for Sale with Low Mileage in Fishkill
