Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPrinceton, IN
206 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:
- 3L I6 Diesel
- Exterior color:
- Gray
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 49,226
- Stock #:
- 234370
- VIN:
- 3GCUDCE85RG306562
Sponsored by Auto House Superstore Inc.
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,226 mi
Terre Haute, IN
77 mi away
Fair Deal
$39,998
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 63,232
- Stock #:
- RG391902
- VIN:
- 3GCUDCED3RG391902
Price drop
-$1,186
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,232 mi
Evansville, IN
27 mi away
Fair Deal
$38,537
$37,351
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 124,735
- Stock #:
- 263145
- VIN:
- 1GCPYCEF4LZ263145
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
124,735 mi
Princeton, KY
86 mi away
Fair Deal
$25,999
- 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:
- 31,678
- Stock #:
- BP4947
- VIN:
- 3GCUKCED2SG118140
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
31,678 mi
Brazil, IN
84 mi away
Fair Deal
$42,744
- 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:
- 7,928
- Stock #:
- BP5033
- VIN:
- 3GCPKCEK0SG133893
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,928 mi
Brazil, IN
84 mi away
Fair Deal
$42,914
- 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:
- 58,310
- Stock #:
- C7426A
- VIN:
- 3GCUDCED4PG303713
New arrival
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,310 mi
Radcliff, KY
97 mi away
Good Deal
$36,999
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 124,735
- Stock #:
- 263145
- VIN:
- 1GCPYCEF4LZ263145
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
124,735 mi
Princeton, KY
86 mi away
Fair Deal
$25,999
- 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:
- 33,893
- Stock #:
- AB1621
- VIN:
- 3GCPDCED9NG585356
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,893 mi
Home delivery from Jefferson City, MO
Price includes $369 shipping
Good Deal
$35,618
- 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:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $987 shipping
Great Deal
$29,972
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 37,230
- Stock #:
- R10624A
- VIN:
- 3GCPDCEK5PG194044
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
37,230 mi
Home delivery from Buford, GA
Price includes $1,250 shipping
Great Deal
$35,030
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 37,400
- Stock #:
- 4750
- VIN:
- 3GCPDCEK6RG233761
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
37,400 mi
Vandalia, IL
91 mi away
Fair Deal
$37,581
- Year:
- 2026
- 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, Cloth seat trim
- Transmission:
- Automatic
- Mileage:
- 2,806
- Stock #:
- 66564A
- VIN:
- 3GCUKCED7TG451970
New arrival
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,806 mi
Evansville, IN
26 mi away
Great Deal
$44,949
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 59,181
- Stock #:
- 260989A
- VIN:
- 3GCPYCEF6KG111804
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,181 mi
Home delivery from Canfield, OH
Price includes $609 shipping
Fair Deal
$31,307
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 55,859
- Stock #:
- F1344A
- VIN:
- 3GCPYCEL1NG100154
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,859 mi
Home delivery from Barrington, IL
Price includes $2,640 shipping
Good Deal
$34,811
- 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:
- Red Hot
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,502
- Stock #:
- R0925
- VIN:
- 3GCPDCEK1RG422205
Price drop
-$780
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,502 mi
Home delivery from Hazard, KY
Price includes $314 shipping
Great Deal
$40,010
$39,230
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,391
- Stock #:
- P010376
- VIN:
- 3GCPDCEK5RG292882
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,391 mi
Home delivery from Zumbrota, MN
Price includes $735 shipping
Good Deal
$36,580
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 136,182
- Stock #:
- T2610529
- VIN:
- 3GCPYCEF4LG198524
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
136,182 mi
Terre Haute, IN
76 mi away
Fair Deal
$24,551
- 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:
- 58,128
- Stock #:
- DC26250
- VIN:
- 1GCPYCEF6KZ273870
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,128 mi
Home delivery from Delphos, OH
Price includes $304 shipping
Fair Deal
$29,899
- Year:
- 2026
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 12,471
- Stock #:
- 2CT7026
- VIN:
- 3GCUKCED7TG347026
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,471 mi
Home delivery from Reidsville, NC
Price includes $640 shipping
Good Deal
$44,489
- 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:
- Cypress Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,309
- Stock #:
- SG371387
- VIN:
- 3GCPKCEK2SG371387
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,309 mi
Home delivery from Columbia, KY
Price includes $302 shipping
Fair Deal
$41,779
- 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:
- Sand Dune Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 74,474
- Stock #:
- 176798
- VIN:
- 3GCUDCED4PG176798
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
74,474 mi
Fairfield, IL
40 mi away
Fair Deal
$35,903
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 150,607
- Stock #:
- 7191A
- VIN:
- 1GCPYCEF2MZ255191
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
150,607 mi
Home delivery from Hazard, KY
Price includes $753 shipping
Great Deal
$21,552
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,986
- Stock #:
- A666A
- VIN:
- 1GCPYCEF6LZ373758
Price drop
-$500
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,986 mi
Home delivery from Dwight, IL
Price includes $292 shipping
Good Deal
$24,641
$24,141
- 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:
- 7,928
- Stock #:
- BP5033
- VIN:
- 3GCPKCEK0SG133893
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,928 mi
Brazil, IN
84 mi away
Fair Deal
$42,914
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Princeton, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,697.77. The average price has decreased by -5.5% since last year. The 196 for sale near Princeton, IN on CarGurus, range from $18,976 to $58,506 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Princeton, IN have no reported accidents or damage?
165 out of 196 for sale near Princeton, IN 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
CarGurus Editorial Team
Best Truck Lease Deals in November 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 November 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.
CarGurus Editorial Team
Car Deals with 0% APR in November 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 Princeton INChevrolet Silverado 1500 RST in Princeton INChevrolet Silverado 1500 LTZ in Princeton INChevrolet Silverado 1500 LT Trail Boss in Princeton INChevrolet Silverado 1500 LT1 in Princeton INChevrolet Silverado 1500 Custom in Princeton INChevrolet Silverado 1500 High Country in Princeton INChevrolet Silverado 1500 Custom Trail Boss in Princeton INChevrolet Silverado 1500 Work Truck in Princeton IN
Chevrolet Silverado 1500 in Evansville INChevrolet Silverado 1500 in Jasper INChevrolet Silverado 1500 in Owensboro KYChevrolet Silverado 1500 in Terre Haute INChevrolet Silverado 1500 in Bloomington INChevrolet Silverado 1500 in Louisville KYChevrolet Silverado 1500 in Carbondale ILChevrolet Silverado 1500 in Paducah KYChevrolet Silverado 1500 in Columbus IN
Chevrolet Silverado 1500 in Princeton INOld Chevy Trucks for Sale in Princeton INClassic Muscle Cars for Sale in Princeton INChevrolet Trucks For Sale in Princeton INCheap Muscle Cars for Sale in Princeton INWork Trucks for Sale in Princeton INReliable Cars For Sale in Princeton INAmerican Made Trucks For Sale in Princeton INBest Pickup Trucks For Sale in Princeton INBest Cars Under $5,000 For Sale in Princeton IN
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 PrincetonUsed SUVs / Crossovers for Sale with Low Mileage in PrincetonUsed Hatchbacks for Sale with Low Mileage in PrincetonUsed Convertibles for Sale with Low Mileage in PrincetonUsed Vans for Sale with Low Mileage in PrincetonUsed Minivans for Sale with Low Mileage in PrincetonUsed Pickup Trucks for Sale with Low Mileage in PrincetonUsed Coupes for Sale with Low Mileage in PrincetonUsed Wagons for Sale with Low Mileage in Princeton
