New Chevrolet Silverado 1500 Custom Trail Boss for Sale nearLongboat Key, FL
153 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:
- 310 hp 2.7L I4
- Exterior color:
- White Sands
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10
- Stock #:
- TG460327
- VIN:
- 3GCPKCEK0TG460327
Sponsored by AutoNation Chevrolet South Clearwater
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Clearwater, FL
37 mi away
New car
MSRP $56,340
$54,084
- 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
- Transmission:
- Automatic
- Mileage:
- 5,794
- Stock #:
- TG229348
- VIN:
- 3GCUKCED9TG229348
New arrival
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Clearwater, FL
37 mi away
New car
MSRP $59,730
$49,089
- 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:
- 1
- Stock #:
- 265885
- VIN:
- 3GCUKCE89TG408797
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Clearwater, FL
43 mi away
New car
MSRP $62,775
$53,540
- 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 $1,350 shipping
New car
MSRP $56,190
$48,963
- 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
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- 6629710
- VIN:
- 3GCUKCED8TG364854
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Lexington, TN
Price includes $1,660 shipping
New car
MSRP $59,280
$51,107
- 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:
- 2
- Stock #:
- TG351884
- VIN:
- 3GCUKCED7TG351884
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Orlando, FL
Price includes $500 shipping
New car
MSRP $60,399
$49,548
- 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:
- 10
- Stock #:
- TG132135
- VIN:
- 3GCUKCED0TG132135
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,465
$39,429
- 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:
- 10
- Stock #:
- TG353319
- VIN:
- 3GCUKCED8TG353319
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 6
- Stock #:
- V3024
- VIN:
- 3GCUKCE86TG408675
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Westminster, MD
Price includes $1,350 shipping
New car
MSRP $58,560
$53,096
- 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:
- 10
- Stock #:
- TG426965
- VIN:
- 3GCUKCEDXTG426965
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 10
- Stock #:
- TG426900
- VIN:
- 3GCUKCED4TG426900
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 10
- Stock #:
- TG426903
- VIN:
- 3GCUKCEDXTG426903
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 10
- Stock #:
- TG261530
- VIN:
- 3GCUKCED4TG261530
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,765
$39,729
- 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 #:
- 268491
- VIN:
- 3GCUKCED9TG347738
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Daytona Beach, FL
Price includes $510 shipping
New car
MSRP $59,700
$48,005
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- G382563
- VIN:
- 3GCUKCE86TG382563
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Jacksonville, FL
Price includes $208 shipping
New car
MSRP $58,285
$50,396
- 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:
- 8
- Stock #:
- 261291
- VIN:
- 3GCUKCED2TG396019
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from East Liverpool, OH
Price includes $2,775 shipping
New car
MSRP $60,054
$51,625
- 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:
- 10
- Stock #:
- TG426482
- VIN:
- 3GCUKCED1TG426482
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 10
- Stock #:
- TG426893
- VIN:
- 3GCUKCED0TG426893
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 10
- Stock #:
- TG431711
- VIN:
- 3GCUKCED4TG431711
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 2
- Stock #:
- TG395923
- VIN:
- 3GCUKCED2TG395923
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Orlando, FL
Price includes $500 shipping
New car
MSRP $62,049
$51,017
- 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 #:
- C00900
- VIN:
- 3GCPKCEK6TG419801
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Reidsville, NC
Price includes $899 shipping
New car
MSRP $54,345
$47,793
- 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:
- 10
- Stock #:
- TG431717
- VIN:
- 3GCUKCED5TG431717
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Miami, FL
Price includes $465 shipping
New car
MSRP $58,490
$39,454
- 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:
- 2
- Stock #:
- TG351485
- VIN:
- 3GCUKCED4TG351485
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Orlando, FL
Price includes $500 shipping
New car
MSRP $60,399
$49,548
- 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:
- 2
- Stock #:
- TG385114
- VIN:
- 3GCUKCED7TG385114
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
Home delivery from Orlando, FL
Price includes $500 shipping
New car
MSRP $60,499
$49,637
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.
Relevant articles
Craig Fitzgerald
The Best Cars to Tow Behind an RV in 2026
Not many new models can be towed behind an RV. We’ve identified several that are recommended for flat-towing according to their owner’s manual, and a few used models that have fewer technological or engineering restrictions.
CarGurus Editorial Team
Car Deals with 0% APR in July 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 Truck Lease Deals in July 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.
