Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearCuddebackville, NY
201 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- White Sands
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,649
- Stock #:
- T67411A
- VIN:
- 3GCPKCEK2TG189755
New arrival
Sponsored by Koch 33 Toyota
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,649 mi
Easton, PA
65 mi away
Fair Deal
$45,701
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 79,241
- Stock #:
- 9T3281
- VIN:
- 1GCPYCEF1MZ261340
Price drop
-$662
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,241 mi
Albany, NY
92 mi away
Fair Deal
$30,787
$30,125
- 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:
- 78,171
- Stock #:
- N12770A
- VIN:
- 3GCPDCEDXNG655737
Price drop
-$998
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
78,171 mi
Washington, NJ
56 mi away
Good Deal
$33,540
$32,542
- 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:
- 100,444
- Stock #:
- 20195999
- VIN:
- 1GCRYCEF2KZ225999
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
100,444 mi
Lehighton, PA
73 mi away
Fair Deal
$24,985
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,054
- Stock #:
- 70253003
- VIN:
- 3GCPDCEKXRG335791
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,054 mi
Store transfer to Wayne, NJ
Price includes $149 shipping
Great Deal
$37,147
- 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
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,626 mi
Albany, NY
94 mi away
Great Deal
$26,500
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,842 mi
Albany, NY
94 mi away
Good Deal
$27,500
- 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:
- 8-Speed Automatic
- Mileage:
- 10,418
- Stock #:
- U20778T
- VIN:
- 3GCPKCEK4SG326516
Price drop
-$2,388
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,418 mi
St James, NY
89 mi away
Great Deal
$41,168
$38,780
- 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:
- Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,046
- Stock #:
- 10T2450
- VIN:
- 3GCPDCEK7NG676916
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,046 mi
Albany, NY
92 mi away
Fair Deal
$32,250
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $4,674 shipping
Fair Deal
$34,637
- 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, Cloth seat trim
- Transmission:
- Automatic
- Mileage:
- 68,302
- Stock #:
- 66644A
- VIN:
- 3GCPDCEK5RG328277
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,302 mi
Englewood, NJ
54 mi away
Good Deal
$33,190
- 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:
- 93,992
- Stock #:
- 144813B
- VIN:
- 1GCPYCEK5NZ144813
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,992 mi
Home delivery from Dallas, TX
Price includes $1,357 shipping
Good Deal
$28,082
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,178
- Stock #:
- C9068209A
- VIN:
- 3GCPYCEF1MG344184
Price drop
-$781
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
81 mi away
Good Deal
$29,064
$28,283
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,769
- Stock #:
- XPA2047
- VIN:
- 1GCPYCEL7NZ128900
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,769 mi
Milford, CT
82 mi away
Fair Deal
$37,359
- 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
- Combined gas mileage:
- 19 MPG
- 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
63 mi away
Good Deal
$35,992
- 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:
- 57,550
- Stock #:
- KZ370333T
- VIN:
- 1GCRYCEF4KZ370333
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,550 mi
Home delivery from Egg Harbor Township, NJ
Price includes $216 shipping
Good Deal
$28,454
- 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:
- Brown
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,430
- Stock #:
- MX5392
- VIN:
- 1GCPYCEF0KZ282600
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,430 mi
Home delivery from Louisville, TN
Price includes $1,154 shipping
Fair Deal
$29,390
- 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:
- Sand Dune Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 17,400
- Stock #:
- C13559
- VIN:
- 3GCPDCED3NG638892
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,400 mi
Freeport, NY
79 mi away
Fair Deal
$38,670
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,533
- Stock #:
- 42511A
- VIN:
- 3GCUDCED9RG350075
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,533 mi
Allentown, PA
79 mi away
Good Deal
$44,485
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $1,277 shipping
Fair Deal
$31,652
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,992
- Stock #:
- CU4125B
- VIN:
- 1GCPYCEF0KZ223191
Price drop
-$828
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,992 mi
Beacon, NY
34 mi away
Good Deal
$26,531
$25,703
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 79,241
- Stock #:
- 9T3281
- VIN:
- 1GCPYCEF1MZ261340
Price drop
-$662
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,241 mi
Albany, NY
92 mi away
Fair Deal
$30,787
$30,125
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $2,095 shipping
Fair Deal
$35,585
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,807
- Stock #:
- M5066
- VIN:
- 3GCPKCEK0SG108461
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,807 mi
Rhinebeck, NY
49 mi away
Fair Deal
$43,075
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Cuddebackville, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,065.49. The average price has decreased by -4.7% since last year. The 153 for sale near Cuddebackville, NY on CarGurus, range from $19,168 to $63,873 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Cuddebackville, NY have no reported accidents or damage?
144 out of 153 for sale near Cuddebackville, 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/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.
Relevant articles
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Cuddebackville NYChevrolet Silverado 1500 RST in Cuddebackville NYChevrolet Silverado 1500 LTZ in Cuddebackville NYChevrolet Silverado 1500 LT Trail Boss in Cuddebackville NYChevrolet Silverado 1500 LT1 in Cuddebackville NYChevrolet Silverado 1500 Custom in Cuddebackville NYChevrolet Silverado 1500 High Country in Cuddebackville NYChevrolet Silverado 1500 Custom Trail Boss in Cuddebackville NYChevrolet Silverado 1500 Work Truck in Cuddebackville NY
Chevrolet Silverado 1500 in Newburgh NYChevrolet Silverado 1500 in New York NYChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in New Brunswick NJChevrolet Silverado 1500 in Wilkes Barre PAChevrolet Silverado 1500 in Allentown PAChevrolet Silverado 1500 in Binghamton NYChevrolet Silverado 1500 in Trenton NJChevrolet Silverado 1500 in New Haven CT
Chevrolet Silverado 1500 in Cuddebackville NYOld Chevy Trucks for Sale in Cuddebackville NYClassic Muscle Cars for Sale in Cuddebackville NYChevrolet Trucks For Sale in Cuddebackville NYCheap Muscle Cars for Sale in Cuddebackville NYWork Trucks for Sale in Cuddebackville NYReliable Cars For Sale in Cuddebackville NYAmerican Made Trucks For Sale in Cuddebackville NYBest Pickup Trucks For Sale in Cuddebackville NYBest Cars Under $5,000 For Sale in Cuddebackville 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 CuddebackvilleUsed SUVs / Crossovers for Sale with Low Mileage in CuddebackvilleUsed Hatchbacks for Sale with Low Mileage in CuddebackvilleUsed Convertibles for Sale with Low Mileage in CuddebackvilleUsed Vans for Sale with Low Mileage in CuddebackvilleUsed Minivans for Sale with Low Mileage in CuddebackvilleUsed Pickup Trucks for Sale with Low Mileage in CuddebackvilleUsed Coupes for Sale with Low Mileage in CuddebackvilleUsed Wagons for Sale with Low Mileage in Cuddebackville
