CarGurus Header
Location:

Include delivery listings?

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Big Pine Key, FL

98 results

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:
Gideon/Very Dark Atmosphere
Transmission:
8-Speed Automatic
Mileage:
44,458
Stock #:
G200216A
VIN:
3GCPDCEK0PG193982
Black 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
Bomnin Chevrolet West Kendall

Sponsored by Bomnin Chevrolet West Kendall

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,458 mi

Miami, FL
87 mi away
Fair Deal

$36,990

Year:
2025
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:
23 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
15,043
Stock #:
1138849A
VIN:
3GCUKCE86SG193605
Summit White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,043 mi

Miami, FL
94 mi away
Fair Deal

$43,490

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
Cherry Red 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,690 mi

Miami, FL
87 mi away
Fair Deal

$27,490

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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
104,662
Stock #:
RN7979Q
VIN:
1GCPYCEL0MZ288387
Shadow Gray Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,662 mi

Miami, FL
87 mi away
Fair Deal

$29,472

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
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,169

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,818 mi

Home delivery from Jacksonville, FL
Price includes $385 shipping
Good Deal

$46,538

$45,369

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
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,560 mi

Home delivery from Scottsdale, AZ
Price includes $2,418 shipping
Fair Deal

$47,016

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
Slate Gray Metallic 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 10-Speed Automatic
Price drop

-$1,025

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

2,325 mi

Home delivery from Delray Beach, FL
Price includes $432 shipping
Great Deal

$47,776

$46,751

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
Mosaic Black Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,771 mi

Home delivery from Seffner, FL
Price includes $246 shipping
Great Deal

$32,730

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
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,000

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,021 mi

Home delivery from Palm Coast, FL
Price includes $949 shipping
Good Deal

$47,139

$46,139

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:
Black
Transmission:
Automatic
Mileage:
14,105
Stock #:
P9991
VIN:
3GCUKCED5SG215235
Slate Gray Metallic 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,105 mi

Home delivery from Jacksonville, FL
Price includes $584 shipping
Fair Deal
Manufacturer certified

$47,412

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
Shadow Gray Metallic 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,746 mi

Home delivery from Orlando, FL
Price includes $260 shipping
Great Deal

$25,957

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
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,768 mi

Home delivery from Pleasantville, NJ
Price includes $2,280 shipping
Good Deal

$37,270

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:
Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
112,557
Stock #:
1213648A
VIN:
3GCPYCEF7MG292818
Blue Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$500

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

112,557 mi

Miami, FL
94 mi away
Good Deal

$24,490

$23,990

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:
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
Summit White 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,331 mi

Home delivery from Jacksonville, FL
Price includes $584 shipping
Good Deal
Manufacturer certified

$35,848

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
Red 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,590 mi

Home delivery from Euless, TX
Price includes $1,656 shipping
Good Deal

$30,651

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
Brown 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

141,315 mi

Home delivery from Orlando, FL
Price includes $331 shipping
Great Deal

$21,321

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:
33,050
Stock #:
RG211760
VIN:
3GCPDCEK4RG211760
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,050 mi

Home delivery from Plant City, FL
Price includes $350 shipping
Fair Deal

$41,342

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:
Cherry Red
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
50,370
Stock #:
A17166N
VIN:
1GCPYCEL2NZ131123
Cherry Red 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,370 mi

Home delivery from Saint Charles, MO
Price includes $1,108 shipping
Fair Deal

$38,429

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
Summit White 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,797 mi

Home delivery from Sykesville, MD
Price includes $1,300 shipping
Fair Deal

$42,594

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:
Gray
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,899
Stock #:
C10309A
VIN:
3GCUKCED6SG208634
Gray 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,899 mi

Home delivery from Sarasota, FL
Price includes $579 shipping
Fair Deal
Manufacturer certified

$44,599

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
Gray 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,322 mi

Home delivery from Arlington, TX
Price includes $1,658 shipping
Fair Deal

$40,660

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:
6,412
Stock #:
G330126A
VIN:
3GCUKCED9SG197256
Summit White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,412 mi

Miami, FL
94 mi away
Fair Deal

$44,490

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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
104,662
Stock #:
RN7979Q
VIN:
1GCPYCEL0MZ288387
Shadow Gray Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,662 mi

Miami, FL
87 mi away
Fair Deal

$29,472

Page 1 of 5

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Big Pine Key, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,251.34. The average price has decreased by -1.5% since last year. The 97 for sale near Big Pine Key, FL on CarGurus, range from $21,321 to $66,690 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Big Pine Key, FL have no reported accidents or damage?
82 out of 97 for sale near Big Pine Key, 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.

A better way to discover your best deal

Let us help you find a car you’ll love.

CarGurus Footer