New Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinchester, IN
168 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:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 15
- Stock #:
- 38103N
- VIN:
- 3GCUKCED5TG463518
Sponsored by Tom Gill Chevrolet
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Florence, KY
83 mi away
New car
MSRP $59,558
$51,157
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5
- Stock #:
- GM6816
- VIN:
- 3GCUKCE80TG274889
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Columbia City, IN
71 mi away
New car
MSRP $60,815
$50,810
- 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:
- 3
- Stock #:
- 60833
- VIN:
- 3GCUKCED3TG425236
Price drop
-$3,000
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Troy, OH
43 mi away
New car
MSRP $61,784
$54,317
$51,317
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- 26595
- VIN:
- 3GCUKCED1TG447509
Price drop
-$2,395
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
McCordsville, IN
52 mi away
New car
MSRP $59,255
$49,181
$46,786
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Mileage:
- 0
- Stock #:
- 26776
- VIN:
- 3GCUKCED6TG480375
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from La Grange, KY
Price includes $183 shipping
New car
MSRP $59,685
$48,967
- 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:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 4
- Stock #:
- 7-507067
- VIN:
- 3GCUKCED0TG507067
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Durand, MI
Price includes $588 shipping
New car
MSRP $58,525
$49,059
- 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:
- White Sands
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- 26546
- VIN:
- 3GCUKCED1TG415689
Price drop
-$2,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
McCordsville, IN
52 mi away
New car
MSRP $60,809
$48,328
$46,328
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- 26584
- VIN:
- 3GCUKCED8TG452190
Price drop
-$3,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
McCordsville, IN
52 mi away
New car
MSRP $58,400
$48,543
$45,543
- 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:
- 5
- Stock #:
- 26LD0739
- VIN:
- 3GCUKCED8TG420940
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lewisville, TX
Price includes $1,242 shipping
New car
MSRP $58,984
$50,461
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- White Sands
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- HCVTG431301
- VIN:
- 3GCUKCE83TG431301
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Noblesville, IN
54 mi away
New car
MSRP $62,189
$51,959
- 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:
- White Sands
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Stock #:
- 261916
- VIN:
- 3GCUKCED6TG505002
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from East Liverpool, OH
Price includes $702 shipping
New car
MSRP $60,414
$49,283
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Summit White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- HCVTG428703
- VIN:
- 3GCUKCE88TG428703
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Noblesville, IN
54 mi away
New car
MSRP $62,189
$51,959
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- C261923
- VIN:
- 3GCUKCED4TG508688
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Cincinnati, OH
68 mi away
New car
MSRP $59,980
$50,737
- 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:
- White Sands
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Stock #:
- 261884
- VIN:
- 3GCUKCED6TG456867
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from East Liverpool, OH
Price includes $702 shipping
New car
MSRP $58,705
$47,813
- 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:
- White Sands
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- 26603
- VIN:
- 3GCUKCED9TG464980
Price drop
-$2,195
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
McCordsville, IN
52 mi away
New car
MSRP $59,810
$49,481
$47,286
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- HCVTG431305
- VIN:
- 3GCUKCE80TG431305
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Noblesville, IN
54 mi away
New car
MSRP $62,189
$51,959
- 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:
- White Sands
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- N26606
- VIN:
- 3GCUKCED3TG509556
Price drop
-$2,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Waynesville, MO
Price includes $1,266 shipping
New car
MSRP $58,340
$49,864
$47,864
- 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:
- 0
- Stock #:
- 51TG508385
- VIN:
- 3GCUKCED8TG508385
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Springfield, OH
63 mi away
New car
MSRP $58,340
$48,239
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- T60761
- VIN:
- 3GCUKCED5TG259835
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Plainfield, IN
79 mi away
New car
MSRP $59,710
$46,584
- 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
- Stock #:
- C435947
- VIN:
- 3GCUKCED9TG435947
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Rockville, MD
Price includes $550 shipping
New car
MSRP $60,795
$51,145
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- 26-451
- VIN:
- 3GCUKCED3TG276312
Price drop
-$2,550
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Wapakoneta, OH
51 mi away
New car
MSRP $58,450
$52,873
$50,323
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- 129504
- VIN:
- 3GCUKCED7TG463603
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Paris, KY
Price includes $212 shipping
New car
MSRP $57,765
$45,784
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- 85511
- VIN:
- 3GCUKCED6TG475371
Price drop
-$4,826
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Mentor, OH
Price includes $327 shipping
New car
MSRP $59,825
$54,600
$49,774
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- T61517
- VIN:
- 3GCUKCED2TG448197
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Plainfield, IN
79 mi away
New car
MSRP $60,205
$45,866
FAQs
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.
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