Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Webster, FL
151 results
- 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
Sponsored by Starling Chevrolet of Orlando
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,584 mi
Orlando, FL
41 mi away
Fair Deal
$45,767
- 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
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,771 mi
Seffner, FL
47 mi away
Fair Deal
$34,484
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 20,692
- Stock #:
- B9342
- VIN:
- 3GCUKCED7SG317491
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
20,692 mi
Ocala, FL
38 mi away
Good Deal
$44,695
- 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
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,839
- Stock #:
- MX4469
- VIN:
- 1GCPYCEF2LZ149662
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,839 mi
Home delivery from Louisville, TN
Price includes $914 shipping
Fair Deal
$30,390
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 55,339
- Stock #:
- MX4446
- VIN:
- 1GCPYCEL1MZ352307
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,339 mi
Home delivery from Louisville, TN
Price includes $914 shipping
Good Deal
$35,390
- Year:
- 2019
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 67,825
- Stock #:
- G293416
- VIN:
- 3GCPYCEH5KG293416
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,825 mi
Home delivery from West Palm Beach, FL
Price includes $272 shipping
Great Deal
$26,166
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 116,709
- Stock #:
- D11212
- VIN:
- 3GCPYCEFXKG115726
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,709 mi
Home delivery from Mt Juliet, TN
Price includes $870 shipping
Good Deal
$24,259
- 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:
- 49,116
- Stock #:
- TT4724A
- VIN:
- 1GCPYCEF5MZ314928
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,116 mi
Ocala, FL
38 mi away
Fair Deal
$36,187
- 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:
- White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 123,697
- Stock #:
- C18221
- VIN:
- 3GCPDCED3NG518221
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
123,697 mi
Home delivery from Athens, TN
Price includes $738 shipping
Fair Deal
$28,238
- 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:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,953
- Stock #:
- O459343
- VIN:
- 3GCPDCEK0RG459343
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
20,953 mi
Clermont, FL
17 mi away
Good Deal
$41,782
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 85,808
- Stock #:
- 16044
- VIN:
- 1GCRYCEF3KZ315436
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
85,808 mi
Home delivery from Dayton, OH
Price includes $1,170 shipping
Fair Deal
$28,616
- 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:
- 2,592
- Stock #:
- G305801A
- VIN:
- 3GCUKCED5TG106307
Price drop
-$2,072
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,592 mi
Tampa, FL
49 mi away
Good Deal
$51,574
$49,502
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,725
- Stock #:
- P13746A
- VIN:
- 3GCPDCEK4PG170463
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
77,725 mi
Home delivery from Roswell, GA
Price includes $788 shipping
Fair Deal
$34,528
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 43,773
- Stock #:
- 28792225
- VIN:
- 3GCPKCEK1SG330099
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,773 mi
Store transfer to Ocala, FL
Price includes $549 shipping
Good Deal
$39,547
- 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:
- 1,045
- Stock #:
- 267853A
- VIN:
- 3GCUKCED4TG226003
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,045 mi
Home delivery from Daytona Beach, FL
Price includes $218 shipping
Good Deal
$51,080
$50,080
- 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 $149 shipping
Fair Deal
$46,639
- 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:
- Silver Ice Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 115,642
- Stock #:
- LG101823
- VIN:
- 3GCPYCEF2LG101823
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
115,642 mi
Winter Park, FL
42 mi away
Good Deal
$26,394
- 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:
- 55,918
- Stock #:
- EA19654B
- VIN:
- 3GCPDCEDXNG687376
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,918 mi
Clermont, FL
17 mi away
Fair Deal
$38,237
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red
- Fuel type:
- Diesel
- Interior color:
- Black
- Mileage:
- 110,590
- Stock #:
- 301317
- VIN:
- 3GCUDCE84PG301317
New arrival
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $1,410 shipping
Good Deal
$30,405
- 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
Seffner, FL
47 mi away
Fair Deal
$34,484
- 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:
- Tangier Orange
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 75,103
- Stock #:
- MZ192550
- VIN:
- 1GCPYCEF6MZ192550
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,103 mi
Brooksville, FL
30 mi away
Good Deal
$32,370
- 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:
- 14,797
- Stock #:
- 150127A_1
- VIN:
- 3GCPDCEK5RG150127
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,797 mi
Home delivery from Sykesville, MD
Price includes $900 shipping
Fair Deal
$43,694
- 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 $178 shipping
Fair Deal
$35,652
- 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:
- 1,687
- Stock #:
- TG105533
- VIN:
- 3GCUKCED9TG105533
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,687 mi
Orlando, FL
41 mi away
Fair Deal
$50,607
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