Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearChester, NY
147 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:
- 8-Speed Automatic
- Mileage:
- 43,307
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
Sponsored by Blasius Mitsubishi
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
45 mi away
Good Deal
$38,369
- 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
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,959 mi
Lake Katrine, NY
45 mi away
Good Deal
$27,674
- 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
Price drop
-$1,001
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
31 mi away
Good Deal
$39,168
$38,167
- 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
Price drop
-$1,001
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
31 mi away
Good Deal
$39,168
$38,167
- 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:
- 46,774
- Stock #:
- S19825A
- VIN:
- 3GCUDCED7RG267941
Price drop
-$1,000
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,774 mi
Home delivery from Newton, NC
Price includes $818 shipping
Good Deal
$41,817
$40,816
- 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
Home delivery from Belford, NJ
Price includes $162 shipping
Fair Deal
$29,138
- 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 $1,079 shipping
Good Deal
$36,568
- 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
45 mi away
Good Deal
$38,369
- 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
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $494 shipping
Great Deal
$29,694
- 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
Home delivery from Linden , NJ
Price includes $75 shipping
Good Deal
$25,874
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,368
- Stock #:
- 12932U
- VIN:
- 1GCPYCEF9MZ402428
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,368 mi
Englewood Cliffs, NJ
37 mi away
Good Deal
$35,745
- 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:
- Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 76,574
- Stock #:
- 26696A
- VIN:
- 3GCPYCEK1NG149426
Price drop
-$1,500
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,574 mi
Lake Katrine, NY
45 mi away
Great Deal
$31,674
$30,174
- 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
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $168 shipping
Great Deal
$34,618
- 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:
- GRY
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 62,918
- Stock #:
- 11258
- VIN:
- 3GCPDCED1NG673222
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,918 mi
Home delivery from Blackwood, NJ
Free home delivery
Good Deal
$35,848
- 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:
- 93,405
- Stock #:
- P233870
- VIN:
- 1GCRYCEF3KZ233870
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
93,405 mi
Home delivery from Charlton, MA
Price includes $130 shipping
Good Deal
$25,536
- 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:
- 33,289
- Stock #:
- MX4598
- VIN:
- 1GCPYCEF4MZ232253
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,289 mi
Home delivery from Michigan Center, MI
Price includes $938 shipping
Fair Deal
$37,871
- 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
Home delivery from Gorham, NH
Price includes $257 shipping
Good Deal
$36,946
- 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
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
40,116 mi
Hawthorne, NJ
27 mi away
Good Deal
$38,348
$37,348
- 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:
- 77,925
- Stock #:
- A9763
- VIN:
- 3GCPYCEF7KG109544
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
77,925 mi
Home delivery from Wolcott, NY
Price includes $185 shipping
Fair Deal
$29,454
- 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:
- 31,779
- Stock #:
- 359054
- VIN:
- 1GCRYCEF9LZ359054
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
31,779 mi
Home delivery from Brunswick, ME
Price includes $276 shipping
Fair Deal
$35,971
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 59,609
- Stock #:
- W167457
- VIN:
- 1GCPYCEF3LZ167457
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,609 mi
Home delivery from West Valley City, UT
Price includes $1,949 shipping
Fair Deal
$33,576
- 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
Home delivery from Old Saybrook, CT
Price includes $147 shipping
Good Deal
$28,690
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,611
- Stock #:
- 3024283A
- VIN:
- 1GCPYCEF6LZ368902
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,611 mi
Home delivery from Raleigh, NC
Price includes $1,125 shipping
Fair Deal
$33,625
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 56,505
- Stock #:
- M4944MV
- VIN:
- 3GCPDCED7NG589129
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
56,505 mi
Rhinebeck, NY
46 mi away
Fair Deal
$38,075
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Chester, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,065.50. The average price has decreased by -1% since last year. The 147 for sale near Chester, NY on CarGurus, range from $22,595 to $56,674 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Chester, NY have no reported accidents or damage?
147 out of 147 for sale near Chester, 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
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.
CarGurus Editorial Team
Best Truck Lease Deals in July 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
CarGurus Editorial Team
Best Car Deals in July 2026
In the market for a new or used car this year? Whether you’re looking to buy or lease, we’ve collated a list of the best car deals available this month.
Chevrolet Silverado 1500 LT in Chester NYChevrolet Silverado 1500 RST in Chester NYChevrolet Silverado 1500 LTZ in Chester NYChevrolet Silverado 1500 LT Trail Boss in Chester NYChevrolet Silverado 1500 LT1 in Chester NYChevrolet Silverado 1500 Custom in Chester NYChevrolet Silverado 1500 High Country in Chester NYChevrolet Silverado 1500 Custom Trail Boss in Chester NYChevrolet Silverado 1500 Work Truck in Chester NY
Chevrolet Silverado 1500 in Newburgh NYChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in New York NYChevrolet Silverado 1500 in New Brunswick NJChevrolet Silverado 1500 in New Haven CTChevrolet Silverado 1500 in Holtsville NYChevrolet Silverado 1500 in Allentown PAChevrolet Silverado 1500 in Trenton NJChevrolet Silverado 1500 in Wilkes Barre PA
Chevrolet Silverado 1500 in Chester NYOld Chevy Trucks for Sale in Chester NYClassic Muscle Cars for Sale in Chester NYChevrolet Trucks For Sale in Chester NYCheap Muscle Cars for Sale in Chester NYWork Trucks for Sale in Chester NYReliable Cars For Sale in Chester NYAmerican Made Trucks For Sale in Chester NYBest Pickup Trucks For Sale in Chester NYBest Cars Under $5,000 For Sale in Chester 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 ChesterUsed SUVs / Crossovers for Sale with Low Mileage in ChesterUsed Hatchbacks for Sale with Low Mileage in ChesterUsed Convertibles for Sale with Low Mileage in ChesterUsed Vans for Sale with Low Mileage in ChesterUsed Minivans for Sale with Low Mileage in ChesterUsed Pickup Trucks for Sale with Low Mileage in ChesterUsed Coupes for Sale with Low Mileage in ChesterUsed Wagons for Sale with Low Mileage in Chester
