Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearNaples, FL
123 vehicles found
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Ash
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 50,237
- Stock #:
- N331344A
- VIN:
- 3GCUDCE83RG121829
New arrival
Sponsored by Bomnin Doral Chrysler Dodge Jeep RAM
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,237 mi
Miami, FL
93 mi away
Fair Deal
$38,990
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 95,690
- Stock #:
- G333813A
- VIN:
- 1GCPYCEF3MZ168545
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,690 mi
Miami, FL
95 mi away
Fair Deal
$27,490
- 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:
- 67,788
- Stock #:
- PG225737
- VIN:
- 3GCPDCEK6PG225737
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,788 mi
Miami, FL
94 mi away
Good Deal
$33,658
- 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:
- 22,420
- Stock #:
- G143386
- VIN:
- 3GCPDCEK5RG143386
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,420 mi
Port Charlotte, FL
66 mi away
Great Deal
$39,542
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 98,291
- Stock #:
- NG192944
- VIN:
- 3GCPYCEK7NG192944
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,291 mi
Nokomis, FL
79 mi away
Fair Deal
$30,125
- 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:
- Mosaic Black Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,771
- Stock #:
- 5048
- VIN:
- 1GCPYCEL5NZ100710
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,771 mi
Home delivery from Seffner, FL
Price includes $147 shipping
Great Deal
$32,141
- 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:
- 19,818
- Stock #:
- G399240A
- VIN:
- 3GCUDCEDXRG445180
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,818 mi
Home delivery from Jacksonville, FL
Price includes $294 shipping
Good Deal
$45,278
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,584
- Stock #:
- 180209T
- VIN:
- 3GCPKCEK9SG180209
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,584 mi
Home delivery from Orlando, FL
Price includes $500 shipping
Fair Deal
$43,668
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 99,746
- Stock #:
- 160815
- VIN:
- 3GCPYCEH1LG262679
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,746 mi
Home delivery from Orlando, FL
Price includes $171 shipping
Good Deal
$25,868
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 2,325
- Stock #:
- PCD7224
- VIN:
- 3GCUKCED9SG296756
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,325 mi
Home delivery from Delray Beach, FL
Price includes $327 shipping
Great Deal
$46,146
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 49,669
- Stock #:
- 28739643
- VIN:
- 1GCPYCEK8NZ237762
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,669 mi
Store transfer to Naples, FL
Price includes $1,499 shipping
Fair Deal
$36,497
- Year:
- 2024
- 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:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 7,021
- Stock #:
- S5221
- VIN:
- 3GCUDCE80RG406004
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,021 mi
Home delivery from Palm Coast, FL
Price includes $749 shipping
Fair Deal
$45,939
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $2,124 shipping
Good Deal
$36,864
- 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:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 133,123
- Stock #:
- 374625
- VIN:
- 1GCRYCEF4KZ374625
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
133,123 mi
Home delivery from Brandon, FL
Price includes $201 shipping
Good Deal
$20,191
- 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:
- 67,788
- Stock #:
- PG225737
- VIN:
- 3GCPDCEK6PG225737
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,788 mi
Miami, FL
94 mi away
Good Deal
$33,658
- 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:
- Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 26,322
- Stock #:
- 48208
- VIN:
- 3GCUDCED4PG360459
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,322 mi
Home delivery from Arlington, TX
Price includes $1,551 shipping
Good Deal
$38,771
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,129
- Stock #:
- 27799389
- VIN:
- 3GCPDCEK2PG304404
New arrival
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,129 mi
Store transfer to Naples, FL
Price includes $249 shipping
Fair Deal
$36,247
- 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:
- Silver
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 5,060
- Stock #:
- 70088560
- VIN:
- 3GCPKCEK3SG329293
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,060 mi
Store transfer to Naples, FL
Price includes $699 shipping
Fair Deal
$45,697
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 46,331
- Stock #:
- P9951
- VIN:
- 3GCPYCEF7MG166331
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,331 mi
Home delivery from Jacksonville, FL
Price includes $448 shipping
Good Deal
$35,612
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,560
- Stock #:
- P25761
- VIN:
- 3GCPKCEK0TG160125
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
3,560 mi
Home delivery from Scottsdale, AZ
Price includes $2,622 shipping
Good Deal
$47,221
$46,221
- 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:
- Brown
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 141,315
- Stock #:
- 435347C
- VIN:
- 3GCPYCEF9MG435347
Price drop
-$1,000
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
141,315 mi
Home delivery from Orlando, FL
Price includes $221 shipping
Great Deal
$21,211
$20,211
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 100,306
- Stock #:
- TG275074A
- VIN:
- 3GCUDCET6NG547741
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,306 mi
Home delivery from Delray Beach, FL
Price includes $327 shipping
Good Deal
$30,171
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 95,178
- Stock #:
- 148558
- VIN:
- 3GCPYCEH9MG148558
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,178 mi
Home delivery from Orlando, FL
Price includes $254 shipping
Great Deal
$27,242
- 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:
- 11,945
- Stock #:
- J260520329T1
- VIN:
- 3GCUDCED8RG329671
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,945 mi
Miami Lakes, FL
94 mi away
Fair Deal
$44,445
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Naples, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,164.21. The average price has decreased by -1.4% since last year. The 125 for sale near Naples, FL on CarGurus, range from $20,191 to $60,323 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Naples, FL have no reported accidents or damage?
123 out of 125 for sale near Naples, FL 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.
Relevant articles
CarGurus Editorial Team
The Best Pickup Trucks of 2026, Ranked
Pickup truck competition is fierce and change is in the air. Electric trucks and compact pickups are hitting the market, providing new choices for both small businesses and weekend adventurers. But which truck suits your needs best?
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Craig Fitzgerald
The Best Trucks Under $25,000 in 2026
New trucks cost more than ever, but the prices of used ones finally seem to be cooling. You still can't find the latest and fanciest full-sizes for budget prices, but fortunately, there are plenty of good trucks under $25,000 these days. Here, we've assembled a list of the best.
Chevrolet Silverado 1500 LT in Naples FLChevrolet Silverado 1500 RST in Naples FLChevrolet Silverado 1500 LTZ in Naples FLChevrolet Silverado 1500 LT Trail Boss in Naples FLChevrolet Silverado 1500 LT1 in Naples FLChevrolet Silverado 1500 Custom in Naples FLChevrolet Silverado 1500 High Country in Naples FLChevrolet Silverado 1500 Custom Trail Boss in Naples FLChevrolet Silverado 1500 Work Truck in Naples FL
Chevrolet Silverado 1500 in Fort Myers FLChevrolet Silverado 1500 in North Port FLChevrolet Silverado 1500 in Sarasota FLChevrolet Silverado 1500 in Sebring FLChevrolet Silverado 1500 in Okeechobee FLChevrolet Silverado 1500 in Homestead FLChevrolet Silverado 1500 in Miami FLChevrolet Silverado 1500 in Fort Lauderdale FLChevrolet Silverado 1500 in Key West FL
Chevrolet Silverado 1500 in Naples FLOld Chevy Trucks for Sale in Naples FLClassic Muscle Cars for Sale in Naples FLChevrolet Trucks For Sale in Naples FLCheap Muscle Cars for Sale in Naples FLWork Trucks for Sale in Naples FLReliable Cars For Sale in Naples FLAmerican Made Trucks For Sale in Naples FLBest Pickup Trucks For Sale in Naples FLBest Cars Under $5,000 For Sale in Naples FL
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 NaplesUsed SUVs / Crossovers for Sale with Low Mileage in NaplesUsed Hatchbacks for Sale with Low Mileage in NaplesUsed Convertibles for Sale with Low Mileage in NaplesUsed Vans for Sale with Low Mileage in NaplesUsed Minivans for Sale with Low Mileage in NaplesUsed Pickup Trucks for Sale with Low Mileage in NaplesUsed Coupes for Sale with Low Mileage in NaplesUsed Wagons for Sale with Low Mileage in Naples
