New Chevrolet Silverado 1500 Custom Trail Boss for Sale nearSimsbury, CT
82 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- C26203
- VIN:
- 3GCUKCED6TG418393
Sponsored by Hamden Chevrolet
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Hamden, CT
35 mi away
New car
MSRP $59,875
$51,374
- 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:
- 6
- Stock #:
- 6122
- VIN:
- 3GCUKCED9TG466115
New arrival
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
West Springfield, MA
19 mi away
New car
MSRP $58,309
$53,004
- 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:
- 9
- Stock #:
- N354832
- VIN:
- 3GCUKCED3TG354832
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Danbury, CT
44 mi away
New car
MSRP $60,545
$49,488
- 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
- Stock #:
- T26211
- VIN:
- 3GCUKCED9TG390718
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Avon, CT
4 mi away
New car
MSRP $58,175
$48,393
- 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 $2,182 shipping
New car
MSRP $58,984
$51,402
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- 263525
- VIN:
- 3GCPKCEK5TG263525
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Westminster, MD
Price includes $406 shipping
New car
MSRP $56,190
$47,844
- 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 #:
- V2935
- VIN:
- 3GCUKCED1TG268516
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Westminster, MD
Price includes $406 shipping
New car
MSRP $57,765
$49,832
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5
- Stock #:
- 449950
- VIN:
- 3GCPKCEK8TG449950
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Cottondale, AL
Price includes $1,497 shipping
New car
MSRP $55,325
$49,922
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2
- Stock #:
- C00899
- VIN:
- 3GCPKCEKXTG419798
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Reidsville, NC
Price includes $742 shipping
New car
MSRP $54,345
$47,636
- 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:
- 5
- Stock #:
- N2200572
- VIN:
- 3GCUKCED5TG461865
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lowell, MA
Price includes $695 shipping
New car
MSRP $59,055
$50,279
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- C00822
- VIN:
- 3GCUKCE82TG348720
Price drop
-$1,100
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Reidsville, NC
Price includes $742 shipping
New car
MSRP $58,285
$52,736
$51,636
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 1
- Stock #:
- C00930
- VIN:
- 3GCPKCEK7TG452919
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Reidsville, NC
Price includes $742 shipping
New car
MSRP $54,345
$47,636
- 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:
- 7
- Stock #:
- C26202
- VIN:
- 3GCUKCED8TG418394
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Hamden, CT
35 mi away
New car
MSRP $59,875
$51,374
- 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:
- 5
- Stock #:
- 26LD0729
- VIN:
- 3GCUKCED7TG419889
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lewisville, TX
Price includes $2,182 shipping
New car
MSRP $58,984
$51,600
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- V2467
- VIN:
- 3GCPKCEKXTG198347
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Westminster, MD
Price includes $406 shipping
New car
MSRP $54,045
$46,782
- 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 #:
- 26LD0743
- VIN:
- 3GCUKCED4TG420708
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lewisville, TX
Price includes $2,182 shipping
New car
MSRP $58,984
$51,600
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 1
- Stock #:
- C00933
- VIN:
- 3GCPKCEK1TG452821
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Reidsville, NC
Price includes $742 shipping
New car
MSRP $54,345
$47,636
- 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
- Stock #:
- 261292
- VIN:
- 3GCUKCED4TG395874
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from East Liverpool, OH
Price includes $1,239 shipping
New car
MSRP $60,054
$49,510
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Stock #:
- 457099
- VIN:
- 3GCPKCEK9TG457099
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lumberton, NJ
Price includes $252 shipping
New car
MSRP $56,869
$49,654
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 10
- Stock #:
- TG385307
- VIN:
- 3GCUKCE83TG385307
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Nanuet, NY
Price includes $205 shipping
New car
MSRP $58,285
$51,665
- 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:
- 7
- Stock #:
- N422560
- VIN:
- 3GCUKCED8TG422560
Price drop
-$1,725
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Danbury, CT
44 mi away
New car
MSRP $57,490
$49,613
$47,888
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8
- Stock #:
- N340129
- VIN:
- 3GCPKCEKXTG340129
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Danbury, CT
44 mi away
New car
MSRP $54,485
$47,284
- 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:
- 9
- Stock #:
- N354832
- VIN:
- 3GCUKCED3TG354832
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Danbury, CT
44 mi away
New car
MSRP $60,545
$49,488
- 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
- Stock #:
- 457499
- VIN:
- 3GCUKCED8TG457499
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lumberton, NJ
Price includes $252 shipping
New car
MSRP $60,694
$52,461
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 (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.
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