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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Millbrook, NY

173 results

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 Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
32,368
Stock #:
12932U
VIN:
1GCPYCEF9MZ402428
Cherry Red Tintcoat 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Maserati & Alfa Romeo of Englewood Cliffs

Sponsored by Maserati & Alfa Romeo of Englewood Cliffs

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,368 mi

Englewood Cliffs, NJ
64 mi away
Good Deal

$35,745

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:
Black
Transmission:
8-Speed Automatic
Mileage:
45,063
Stock #:
N12692A
VIN:
3GCPKCEK5SG103787
Summit White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,063 mi

Washington, NJ
99 mi away
Good Deal
Manufacturer certified

$39,540

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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
125,117
Stock #:
CU378338
VIN:
1GCPYCEF0KZ378338
Summit White 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,117 mi

Middletown, CT
55 mi away
Fair Deal

$26,219

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:
Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
13,777
Stock #:
T9451A
VIN:
3GCPDCEK7PG167623
Blue Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,777 mi

Vernon Rockville, CT
62 mi away
Good Deal
Manufacturer certified

$40,912

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 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Home delivery from Louisville, TN
Price includes $1,247 shipping
Good Deal

$35,723

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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
104,108
Stock #:
332395C01
VIN:
1GCPYCEF2KZ332395
Shadow Gray Metallic 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,108 mi

Linden , NJ
86 mi away
Good Deal

$25,799

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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
58,147
Stock #:
U23550
VIN:
1GCPYCEL6MZ371564
White 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,490

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,147 mi

Riverhead, NY
78 mi away
Good Deal

$36,204

$34,714

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:
27,429
Stock #:
20001MA4
VIN:
3GCPDCED6NG585931
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,429 mi

North Haven, CT
50 mi away
Good Deal

$37,987

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:
26,678
Stock #:
19864MA3
VIN:
3GCUDCED0RG316140
Summit White 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,678 mi

North Haven, CT
50 mi away
Good Deal

$41,181

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:
35,936
Stock #:
28519465
VIN:
3GCPDCEK2PG188511
Black 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,936 mi

Store transfer to Waterbury, CT
Price includes $299 shipping
Fair Deal

$39,297

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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,812
Stock #:
A6979A
VIN:
3GCPYCEF1LG177419
Cajun Red Tintcoat 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,812 mi

Brattleboro, VT
95 mi away
Good Deal

$31,629

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:
Blue
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
17,718
Stock #:
U23215
VIN:
3GCUDCEDXRG115166
Blue 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,718 mi

Riverhead, NY
78 mi away
Good Deal

$43,204

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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
97,904
Stock #:
0201A
VIN:
1GCPYCEFXLZ133175
Shadow Gray Metallic 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

97,904 mi

Home delivery from Pen Argyl, PA
Price includes $420 shipping
Good Deal

$27,810

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Dark Ash Metallic
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
29,769
Stock #:
T52696B
VIN:
3GCUDCE87RG153960
Dark Ash Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,769 mi

Pittsfield, MA
51 mi away
Great Deal

$41,161

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:
Jet Black
Transmission:
10-Speed Automatic
Mileage:
102,783
Stock #:
5211
VIN:
3GCPYCEF9MG436837
Blue 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 10-Speed Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,783 mi

Old Saybrook, CT
74 mi away
Fair Deal

$28,543

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:
Jet Black
Transmission:
Automatic
Mileage:
113,737
Stock #:
275538
VIN:
3GCPYCEF6LG275538
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

113,737 mi

Windsor Locks, CT
54 mi away
Good Deal

$23,995

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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
Automatic
Mileage:
79,727
Stock #:
N355141
VIN:
1GCRYCEH4LZ355141
Gray 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

79,727 mi

Home delivery from Barre, VT
Price includes $266 shipping
Good Deal

$26,560

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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
104,500
Stock #:
184422C01
VIN:
1GCPYCEF3LZ184422
Summit White 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,500 mi

South Amboy, NJ
95 mi away
Great Deal

$23,399

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
65,987
Stock #:
CC2995
VIN:
1GCPYCEF2LZ262639
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,987 mi

Bristol, CT
41 mi away
Great Deal

$29,096

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:
Jet Black
Transmission:
Automatic
Mileage:
16,821
Stock #:
A146227
VIN:
3GCUKCED0SG146227
Gray 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,821 mi

Lebanon, NJ
98 mi away
Fair Deal

$48,537

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:
Black
Transmission:
8-Speed Automatic
Mileage:
45,063
Stock #:
N12692A
VIN:
3GCPKCEK5SG103787
Summit White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,063 mi

Washington, NJ
99 mi away
Good Deal
Manufacturer certified

$39,540

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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
125,117
Stock #:
CU378338
VIN:
1GCPYCEF0KZ378338
Summit White 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,117 mi

Middletown, CT
55 mi away
Fair Deal

$26,219

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:
3,648
Stock #:
A216583
VIN:
3GCUKCED0SG216583
Slate Gray Metallic 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,000

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,648 mi

Pawling, NY
18 mi away
Fair Deal

$48,675

$47,675

Page 1 of 8

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Millbrook, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,260.25. The average price has decreased by -1.7% since last year. The 131 for sale near Millbrook, NY on CarGurus, range from $20,900 to $67,098 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Millbrook, NY have no reported accidents or damage?
131 out of 131 for sale near Millbrook, NY 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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