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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Winchendon, MA

188 results
Winchendon, MA
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Denooyer Chevrolet

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,773 miles

$29,908

Great Deal
Albany, NY
89 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:
Gray (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
71,773
Stock number:
43146
VIN:
1GCPYCEF5MZ260840

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,635 miles

$46,924

Fair Deal
Raynham, MA
74 mi away
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:
Cypress Gray
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
1,635
Stock number:
M0131A
VIN:
3GCUKCED8SG339385

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,962 miles

$31,153

Good Deal
Albany, NY
89 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:
Northsky Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
63,962
Stock number:
43179
VIN:
1GCPYCEF0MZ386247

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,417 miles

$30,655

Good Deal
Old Saybrook, CT
95 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
51,417
Stock number:
N1140K
VIN:
1GCPYCEF5KZ412192

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,464 miles

$29,997

Good Deal
Old Saybrook, CT
95 mi away
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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
41,464
Stock number:
AC9274
VIN:
3GCPYCEH7KG164593

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,082 miles

$31,769

Great Deal
Albany, NY
89 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
42,082
Stock number:
42956
VIN:
1GCPYCEF5MZ376961

Preparing for a close up...

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,728 miles

$28,995

Good Deal
Acton, MA
34 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
79,728
Stock number:
A25714A
VIN:
1GCPYCEF5LZ354036

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,230 miles

$27,995

Good Deal
Fair Haven, VT
89 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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
79,230
Stock number:
268675
VIN:
3GCPYCEF5KG268675

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

102,103 miles

$23,500

Good Deal
Framingham, MA
40 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,103
Stock number:
C34140A
VIN:
1GCRYCEF1KZ246584

Preparing for a close up...

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,773 miles

$29,908

Great Deal
Albany, NY
89 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:
Gray (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
71,773
Stock number:
43146
VIN:
1GCPYCEF5MZ260840

Preparing for a close up...

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

126,232 miles

$21,995

Fair Deal
Rochdale, MA
33 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:
Summit White
Fuel type:
Gasoline
Transmission:
6-Speed Automatic
Mileage:
126,232
Stock number:
4432
VIN:
1GCRYCEF8KZ344432

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,783 miles

$19,995

Great Deal
Tilton, NH
61 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:
Silver
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
133,783
Stock number:
75
VIN:
3GCPYCEF2KG141396

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,962 miles

$31,153

Good Deal
Albany, NY
89 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:
Northsky Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
63,962
Stock number:
43179
VIN:
1GCPYCEF0MZ386247

Preparing for a close up...

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,086 miles

$30,999

Good Deal
Hudson, NY
89 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,086
Stock number:
2200P
VIN:
1GCPYCEF7MZ408339

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,277 miles

$35,987

Good Deal
Certified Pre-Owned
Concord, NH
46 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
40,277
Stock number:
T58572A
VIN:
1GCPYCEF0MZ158572

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,195 miles

$31,990

Great Deal
Malden, MA
54 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
44,195
Stock number:
C14811
VIN:
3GCPYCEK3NG116041

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,844 miles

$27,700

Good Deal
Westborough, MA
33 mi away
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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
78,844
Stock number:
T78329B
VIN:
3GCPYCEF8LG442157

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,144 miles

$39,990

Good Deal
Norwood, MA
55 mi away
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:
38,144
Stock number:
U2400050
VIN:
3GCUDCED3RG248660

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,665 miles

$27,995

Good Deal
Greenwich, NY
81 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
89,665
Stock number:
U10705
VIN:
1GCPYCEF7KZ385691

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,107 miles

$39,995

Fair Deal
Certified Pre-Owned
Ballston Spa, NY
94 mi away
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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,107
Stock number:
90226B
VIN:
3GCUDCEDXPG332214

Preparing for a close up...

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,277 miles

$35,987

Good Deal
Certified Pre-Owned
Concord, NH
46 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
40,277
Stock number:
T58572A
VIN:
1GCPYCEF0MZ158572

Sponsored

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