Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearOlivebridge, NY
197 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,302
- Stock #:
- 17332
- VIN:
- 1GCPYCEF2LZ169720
Sponsored by Road Ready Used Cars
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,302 mi
Ansonia, CT
73 mi away
Fair Deal
$32,988
- 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
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
78,171 mi
Washington, NJ
89 mi away
Fair Deal
$35,540
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 7,819
- Stock #:
- A279698
- VIN:
- 3GCUKCED2SG279698
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,819 mi
Pawling, NY
44 mi away
Fair Deal
$46,000
- 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:
- 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
65 mi away
Fair Deal
$19,299
- 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
Price drop
-$1,000
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,506 mi
Brodheadsville, PA
91 mi away
Good Deal
$44,488
$43,488
- 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:
- 53,114
- Stock #:
- G26441A
- VIN:
- 3GCUDCED6RG140842
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,114 mi
Bartonsville, PA
82 mi away
Good Deal
$39,353
- 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:
- Cajun Red Tintcoat
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 24,311
- Stock #:
- G4651A
- VIN:
- 1GCRYCEF6KZ299295
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
24,311 mi
Utica, NY
98 mi away
Great Deal
$30,939
- 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
89 mi away
Good Deal
$27,994
- 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
90 mi away
Great Deal
$24,799
$23,799
- 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:
- 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 $395 shipping
Good Deal
$30,068
- 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
89 mi away
Fair Deal
$42,558
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,712
- Stock #:
- C260731522T1
- VIN:
- 3GCUDCED6RG182458
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,712 mi
Home delivery from Rochester, NY
Price includes $186 shipping
Good Deal
$41,738
- 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:
- 91,842
- Stock #:
- 43999
- VIN:
- 3GCPYCEF3MG435456
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,842 mi
Albany, NY
61 mi away
Fair Deal
$31,175
- 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
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,389 mi
Ballston Spa, NY
77 mi away
Fair Deal
$29,975
- 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
88 mi away
Good Deal
$28,644
- 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:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 86,910
- Stock #:
- 10187
- VIN:
- 1GCRYCEF8LZ308628
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
86,910 mi
Home delivery from Yakima, WA
Price includes $3,408 shipping
Fair Deal
$30,264
- 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:
- 104,500
- Stock #:
- 184422C01
- VIN:
- 1GCPYCEF3LZ184422
Price drop
-$1,000
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,500 mi
Linden , NJ
90 mi away
Great Deal
$23,799
$22,799
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 64,109
- Stock #:
- 8689
- VIN:
- 1GCRYCEF5KZ313123
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
64,109 mi
Home delivery from Willimantic, CT
Price includes $300 shipping
Fair Deal
$29,984
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 22,873
- Stock #:
- 402210
- VIN:
- 3GCPDCEK4RG402210
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,873 mi
Home delivery from Orlando, FL
Price includes $1,003 shipping
Fair Deal
$43,390
- Year:
- 2023
- 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:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 48,518
- Stock #:
- 5153
- VIN:
- 3GCUDCED9PG302640
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,518 mi
Home delivery from Seffner, FL
Price includes $1,114 shipping
Great Deal
$36,106
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
64 mi away
Good Deal
$30,698
- 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
97 mi away
Fair Deal
$42,950
- 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
75 mi away
Good Deal
$32,774
- 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
54 mi away
Good Deal
$37,986
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Olivebridge, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,829.95. The average price has decreased by -0.6% since last year. The 142 for sale near Olivebridge, NY on CarGurus, range from $22,119 to $68,611 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Olivebridge, NY have no reported accidents or damage?
123 out of 142 for sale near Olivebridge, 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.
Relevant articles
CarGurus Editorial Team
Best Truck Lease Deals in August 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
Car Deals with 0% APR in August 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 Car Deals in August 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 Olivebridge NYChevrolet Silverado 1500 RST in Olivebridge NYChevrolet Silverado 1500 LTZ in Olivebridge NYChevrolet Silverado 1500 LT Trail Boss in Olivebridge NYChevrolet Silverado 1500 LT1 in Olivebridge NYChevrolet Silverado 1500 Custom in Olivebridge NYChevrolet Silverado 1500 High Country in Olivebridge NYChevrolet Silverado 1500 Custom Trail Boss in Olivebridge NYChevrolet Silverado 1500 Work Truck in Olivebridge NY
Chevrolet Silverado 1500 in Newburgh NYChevrolet Silverado 1500 in Albany NYChevrolet Silverado 1500 in Pittsfield MAChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in New Haven CTChevrolet Silverado 1500 in Hartford CTChevrolet Silverado 1500 in New York NYChevrolet Silverado 1500 in Chicopee MAChevrolet Silverado 1500 in Binghamton NY
Chevrolet Silverado 1500 in Olivebridge NYOld Chevy Trucks for Sale in Olivebridge NYClassic Muscle Cars for Sale in Olivebridge NYChevrolet Trucks For Sale in Olivebridge NYCheap Muscle Cars for Sale in Olivebridge NYWork Trucks for Sale in Olivebridge NYReliable Cars For Sale in Olivebridge NYAmerican Made Trucks For Sale in Olivebridge NYBest Pickup Trucks For Sale in Olivebridge NYBest Cars Under $5,000 For Sale in Olivebridge 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 OlivebridgeUsed SUVs / Crossovers for Sale with Low Mileage in OlivebridgeUsed Hatchbacks for Sale with Low Mileage in OlivebridgeUsed Convertibles for Sale with Low Mileage in OlivebridgeUsed Vans for Sale with Low Mileage in OlivebridgeUsed Minivans for Sale with Low Mileage in OlivebridgeUsed Pickup Trucks for Sale with Low Mileage in OlivebridgeUsed Coupes for Sale with Low Mileage in OlivebridgeUsed Wagons for Sale with Low Mileage in Olivebridge
