CarGurus Header
Location:

Include delivery listings?

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Destin, FL

135 results

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Sand Dune Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,490
Stock #:
TNG574292
VIN:
3GCPDCEK0NG574292
Sand Dune Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Step One Chrysler Dodge Jeep Ram Crestview

Sponsored by Step One Chrysler Dodge Jeep Ram Crestview

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,490 mi

Crestview, FL
22 mi away
Fair Deal

$32,861

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:
Jet Black
Transmission:
Automatic
Mileage:
4,205
Stock #:
H14508A
VIN:
3GCUKCE81SG110176
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,205 mi

Panama City, FL
49 mi away
Fair Deal

$47,873

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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
60,596
Stock #:
UF2633
VIN:
1GCPYCEL2NZ117108
Shadow Gray Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,596 mi

Ozark, AL
87 mi away
Good Deal

$35,976

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
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Home delivery from Louisville, TN
Price includes $722 shipping
Great Deal

$35,198

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
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,725 mi

Home delivery from Roswell, GA
Price includes $562 shipping
Great Deal

$34,302

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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
60,596
Stock #:
UF2633
VIN:
1GCPYCEL2NZ117108
Shadow Gray Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,596 mi

Ozark, AL
87 mi away
Good Deal

$35,976

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
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Home delivery from Louisville, TN
Price includes $722 shipping
Good Deal

$30,198

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:
Gray
Fuel type:
Gasoline
Mileage:
93,416
Stock #:
313326
VIN:
1GCRYCEF8KZ313326
Gray 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive
Price drop

-$2,500

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

93,416 mi

Home delivery from Marietta, GA
Price includes $404 shipping
Fair Deal

$30,222

$27,722

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 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

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

$47,439

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 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,797 mi

Home delivery from Sykesville, MD
Price includes $900 shipping
Good Deal

$43,694

$42,694

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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
32,522
Stock #:
T5113342B
VIN:
3GCPKCEK9SG338001
Sterling Gray Metallic 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,522 mi

Daphne, AL
85 mi away
Fair Deal

$43,968

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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,212
Stock #:
N26199A
VIN:
3GCPYCEF2MG483594
Gray (Satin Steel Metallic) 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,212 mi

Andalusia, AL
63 mi away
Fair Deal

$30,990

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:
Red
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
48,045
Stock #:
NZ236079
VIN:
1GCPYCEL2NZ236079
Red 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,045 mi

Home delivery from Union City, GA
Price includes $864 shipping
Good Deal

$38,078

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:
Gray
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
62,195
Stock #:
28488039
VIN:
3GCPYCEF2MG292628
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,195 mi

Store transfer to Pensacola, FL
Price includes $1,399 shipping
Fair Deal

$37,397

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
Fuel type:
Gasoline
Transmission:
6-Speed Automatic
Mileage:
46,199
Stock #:
232880
VIN:
1GCPYCEF5MZ234836
Blue 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,199 mi

Home delivery from Terre Haute, IN
Price includes $621 shipping
Fair Deal

$35,844

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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
87,128
Stock #:
A1219
VIN:
1GCPYCEF4MZ250624
Blue 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

87,128 mi

Home delivery from Chattanooga, TN
Price includes $660 shipping
Fair Deal

$32,914

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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
63,070
Stock #:
128692
VIN:
3GCPDCEK7PG128692
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic Overdrive
New arrival

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,070 mi

Home delivery from Smyrna, GA
Price includes $266 shipping
Good Deal

$34,261

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
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,775
Stock #:
5019
VIN:
1GCPYCEF0LZ168095
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,775 mi

Home delivery from Burton, MI
Price includes $883 shipping
Great Deal

$30,233

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 Custom Trail Boss Crew Cab 4WD 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 $316 shipping
Great Deal

$34,310

Year:
2021
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:
6-Speed Automatic Overdrive
Mileage:
82,047
Stock #:
MP4710
VIN:
1GCPYCEHXMZ220514
Shadow Gray Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,047 mi

Home delivery from Montgomery, AL
Free home delivery
Good Deal

$30,885

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
White 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

123,697 mi

Home delivery from Athens, TN
Price includes $548 shipping
Good Deal

$28,048

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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,212
Stock #:
N26199A
VIN:
3GCPYCEF2MG483594
Gray (Satin Steel Metallic) 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,212 mi

Andalusia, AL
63 mi away
Fair Deal

$30,990

Page 1 of 6

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Destin, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,276.91. The average price has decreased by -1.9% since last year. The 140 for sale near Destin, FL on CarGurus, range from $22,310 to $65,894 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Destin, FL have no reported accidents or damage?
134 out of 140 for sale near Destin, 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