Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPortland, IN
229 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 92,912
- Stock #:
- VC26183
- VIN:
- 1GCPYCEFXKZ269806
Sponsored by Jim Schmidt Chevrolet
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,912 mi
Hicksville, OH
61 mi away
Fair Deal
$28,605
- 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:
- Red Hot
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 17,414
- Stock #:
- 261579A
- VIN:
- 3GCUKCED1SG339177
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,414 mi
Indianapolis, IN
81 mi away
Fair Deal
$44,999
- 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:
- 83,964
- Stock #:
- C26460A
- VIN:
- 1GCPYCEF2MZ364900
Price drop
-$978
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,964 mi
Avon, IN
86 mi away
Great Deal
$29,730
$29,014
- 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:
- Automatic
- Mileage:
- 35,007
- Stock #:
- 260571A
- VIN:
- 3GCPDCEK3RG234513
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,007 mi
Lebanon, OH
79 mi away
Good Deal
$37,839
- 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:
- 83,964
- Stock #:
- C26460A
- VIN:
- 1GCPYCEF2MZ364900
Price drop
-$978
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,964 mi
Avon, IN
86 mi away
Great Deal
$29,730
$29,014
- 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 $915 shipping
Great Deal
$34,907
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Slate Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 52,778
- Stock #:
- B19182A
- VIN:
- 3GCUDCE8XRG358530
Price drop
-$849
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,778 mi
Anderson, IN
42 mi away
Great Deal
$37,589
$36,740
- 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:
- 51,156
- Stock #:
- P8991A
- VIN:
- 3GCPDCED7NG624218
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,156 mi
Cincinnati, OH
83 mi away
Good Deal
$35,047
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Exterior color:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 72,677
- Stock #:
- 10776
- VIN:
- 3GCPYCEL3MG438489
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
72,677 mi
Akron, IN
69 mi away
Great Deal
$29,900
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 80,076
- Stock #:
- A263367A
- VIN:
- 3GCPYCEF5KG189796
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,076 mi
Tipton, IN
61 mi away
Fair Deal
$30,640
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 5,513
- Stock #:
- P26291B
- VIN:
- 3GCUDCED1RG183839
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,513 mi
Fort Wayne, IN
49 mi away
Fair Deal
$44,260
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 46,365
- Stock #:
- P1208
- VIN:
- 1GCPYCEF9MZ293789
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,365 mi
Home delivery from Middlesboro, KY
Price includes $538 shipping
Fair Deal
$36,137
- 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
Hicksville, OH
61 mi away
Great Deal
$30,340
- 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:
- 113,887
- Stock #:
- E260597A
- VIN:
- 1GCPYCEF0LZ261005
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
113,887 mi
Beavercreek Township, OH
71 mi away
Good Deal
$25,989
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Sand Dune Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,240
- Stock #:
- C16139
- VIN:
- 3GCUDCET0NG535858
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,240 mi
Dayton, OH
69 mi away
Fair Deal
$36,693
- 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:
- 39,306
- Stock #:
- AT6263
- VIN:
- 1GCPYCEFXMZ368466
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,306 mi
West Chester, OH
83 mi away
Good Deal
$35,098
- 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 (Charcoal)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 135,132
- Stock #:
- 250850
- VIN:
- 1GCPYCEF4LZ250850
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
135,132 mi
Home delivery from Salt Lake City, UT
Price includes $2,112 shipping
Fair Deal
$24,012
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,316
- Stock #:
- 26623X
- VIN:
- 3GCPDCEK7RG339815
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,316 mi
Defiance, OH
69 mi away
Fair Deal
$36,350
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,093
- Stock #:
- HCVPPG361993
- VIN:
- 3GCUDCED7PG361993
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,093 mi
Noblesville, IN
60 mi away
Good Deal
$39,963
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,042
- Stock #:
- UCP1843
- VIN:
- 3GCUKCED7SG119803
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,042 mi
Home delivery from Carrollton, KY
Price includes $305 shipping
Great Deal
$44,003
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,319
- Stock #:
- 260883A
- VIN:
- 3GCPKCEK1TG191626
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,319 mi
Home delivery from Canfield, OH
Price includes $334 shipping
Good Deal
$42,733
$41,732
- 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 $189 shipping
Great Deal
$29,089
- 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:
- 76,685
- Stock #:
- 52361T
- VIN:
- 1GCPYCEFXMZ395392
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,685 mi
Dayton, OH
61 mi away
Good Deal
$31,898
- 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:
- Automatic
- Mileage:
- 35,007
- Stock #:
- 260571A
- VIN:
- 3GCPDCEK3RG234513
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,007 mi
Lebanon, OH
79 mi away
Good Deal
$37,839
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Portland, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,761.35. The average price has decreased by -0.8% since last year. The 197 for sale near Portland, IN on CarGurus, range from $21,324 to $66,367 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Portland, IN have no reported accidents or damage?
178 out of 197 for sale near Portland, 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 (or EV battery range).
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 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 Portland INChevrolet Silverado 1500 RST in Portland INChevrolet Silverado 1500 LTZ in Portland INChevrolet Silverado 1500 LT Trail Boss in Portland INChevrolet Silverado 1500 LT1 in Portland INChevrolet Silverado 1500 Custom in Portland INChevrolet Silverado 1500 High Country in Portland INChevrolet Silverado 1500 Custom Trail Boss in Portland INChevrolet Silverado 1500 Work Truck in Portland IN
Chevrolet Silverado 1500 in Anderson INChevrolet Silverado 1500 in Fort Wayne INChevrolet Silverado 1500 in Lima OHChevrolet Silverado 1500 in Kokomo INChevrolet Silverado 1500 in Dayton OHChevrolet Silverado 1500 in Indianapolis INChevrolet Silverado 1500 in Cincinnati OHChevrolet Silverado 1500 in Columbus INChevrolet Silverado 1500 in Marion OH
Chevrolet Silverado 1500 in Portland INOld Chevy Trucks for Sale in Portland INClassic Muscle Cars for Sale in Portland INChevrolet Trucks For Sale in Portland INCheap Muscle Cars for Sale in Portland INWork Trucks for Sale in Portland INReliable Cars For Sale in Portland INAmerican Made Trucks For Sale in Portland INBest Pickup Trucks For Sale in Portland INBest Cars Under $5,000 For Sale in Portland 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 PortlandUsed SUVs / Crossovers for Sale with Low Mileage in PortlandUsed Hatchbacks for Sale with Low Mileage in PortlandUsed Convertibles for Sale with Low Mileage in PortlandUsed Vans for Sale with Low Mileage in PortlandUsed Minivans for Sale with Low Mileage in PortlandUsed Pickup Trucks for Sale with Low Mileage in PortlandUsed Coupes for Sale with Low Mileage in PortlandUsed Wagons for Sale with Low Mileage in Portland
