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

150 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
17,541
Stock #:
L155274A
VIN:
3GCPKCEK4SG277429
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival
Central Florida Chrysler Dodge Jeep RAM

Sponsored by Central Florida Chrysler Dodge Jeep RAM

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,541 mi

Orlando, FL
37 mi away
Fair Deal

$46,084

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
69,165
Stock #:
T7117A
VIN:
3GCUDCED9RG103042
Summit White 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,165 mi

Eustis, FL
22 mi away
Fair Deal

$38,526

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:
40,249
Stock #:
COF260754A
VIN:
3GCPDCEK5PG312349
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,249 mi

Orange City, FL
48 mi away
Good Deal

$36,599

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
Summit White 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

49,116 mi

Ocala, FL
38 mi away
Fair Deal
Manufacturer certified

$36,187

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
White 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

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:
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
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,953 mi

Clermont, FL
17 mi away
Good Deal

$41,782

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
Summit White 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

55,918 mi

Clermont, FL
17 mi away
Fair Deal

$38,237

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
Black 2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
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:
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
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

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:
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
Slate Gray Metallic 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,584 mi

Orlando, FL
41 mi away
Fair Deal
Manufacturer certified

$45,767

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 $914 shipping
Good Deal

$35,390

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 $788 shipping
Fair Deal

$34,528

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
82,742
Stock #:
67199A
VIN:
3GCPDCED1NG658591
Black 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

82,742 mi

Home delivery from Jacksonville, FL
Price includes $36 shipping
Good Deal

$32,562

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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
58,880
Stock #:
TT4758A
VIN:
3GCPKCEK9SG249335
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,880 mi

Ocala, FL
38 mi away
Fair Deal
Manufacturer certified

$38,687

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

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,642 mi

Winter Park, FL
42 mi away
Good Deal

$26,394

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 $914 shipping
Fair Deal

$30,390

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 $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:
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 $991 shipping
Good Deal

$30,341

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
Fair 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black Cloth Seat Trim
Transmission:
Automatic
Mileage:
22,274
Stock #:
35361AT
VIN:
3GCPKCEK6SG154263
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

22,274 mi

Deland, FL
49 mi away
Good Deal

$42,377

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FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Webster, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,269.71. The average price has decreased by -2% since last year. The 153 for sale near Webster, FL on CarGurus, range from $19,990 to $66,432 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Webster, FL have no reported accidents or damage?
148 out of 153 for sale near Webster, 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.

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