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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Poolesville, MD

161 results
Poolesville, MD
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Lindsay Chevrolet of Woodbridge

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,304 miles

$36,500

Good Deal
Woodbridge, VA
35 mi away
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:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,304
Stock number:
HP9569
VIN:
3GCPDCEK3PG311751

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,376 miles

$35,676

Fair Deal
Leesburg, VA
8 mi away
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:
Black
Transmission:
8-Speed Automatic
Mileage:
54,376
Stock number:
P333180
VIN:
3GCPDCEK4RG333180

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,453 miles

$27,300

Great Deal
Waynesboro, PA
45 mi away
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:
Black
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,453
Stock number:
U17211
VIN:
3GCPYCEH8MG351778

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,314 miles

$25,999

Good Deal
Waynesboro, PA
45 mi away
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:
Gray (Satin Steel Metallic)
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
99,314
Stock number:
U17153
VIN:
1GCPYCEH7MZ337631

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$29,500

Good Deal
Waynesboro, PA
43 mi away
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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,679
Stock number:
B34452
VIN:
1GCPYCEK9NZ119607

Preparing for a close up...

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,304 miles

$36,500

Good Deal
Woodbridge, VA
35 mi away
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:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,304
Stock number:
HP9569
VIN:
3GCPDCEK3PG311751

Preparing for a close up...

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,784 miles

$31,458

Fair Deal
Leesburg, VA
7 mi away
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:
1WT/1CX/2CX-Cloth, Jet Black, Interior Trim
Transmission:
Automatic
Mileage:
64,784
Stock number:
LT0379A
VIN:
1GCPYCEF6KZ426179

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,453 miles

$27,300

Great Deal
Waynesboro, PA
45 mi away
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:
Black
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,453
Stock number:
U17211
VIN:
3GCPYCEH8MG351778

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,919 miles

$29,495

Fair Deal
Frederick, MD
21 mi away
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:
41w
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
"black"
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,919
Stock number:
LE48390A
VIN:
1GCPYCEF1KZ242543

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,470 miles

$22,995

Great Deal
Stafford, VA
42 mi away
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
Interior color:
Gray
Mileage:
133,470
Stock number:
DMV1729
VIN:
3GCPYCEF1MG260401

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$33,000

Good Deal
Silver Spring, MD
25 mi away
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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,336
Stock number:
A10858
VIN:
1GCPYCEFXMZ264883

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,485 miles

$35,499

Great Deal
Baltimore, MD
49 mi away
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:
Red Hot
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
14,485
Stock number:
C260194A
VIN:
1GCPYCEF4MZ265821

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,737 miles

$35,877

Fair Deal
Hagerstown, MD
37 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
38,737
Stock number:
LA20954A
VIN:
3GCPDCEK3NG534501

Preparing for a close up...

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,589 miles

$39,156

Fair Deal
Thurmont, MD
35 mi away
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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
29,589
Stock number:
D260004B
VIN:
3GCPDCEK5RG168496

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,314 miles

$25,999

Good Deal
Waynesboro, PA
45 mi away
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:
Gray (Satin Steel Metallic)
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
99,314
Stock number:
U17153
VIN:
1GCPYCEH7MZ337631

Sponsored

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