Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Red Oak, VA
201 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,501
- Stock #:
- 7007182A
- VIN:
- 3GCPDCEK1NG607137
Sponsored by Sanford Imports
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,501 mi
Sanford, NC
91 mi away
Good Deal
$34,770
- 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:
- 30,724
- Stock #:
- 307401B
- VIN:
- 1GCPYCEF2MZ347210
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,724 mi
Kernersville, NC
86 mi away
Good Deal
$37,000
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,741
- Stock #:
- 363238A
- VIN:
- 1GCPYCEF1MZ393238
New arrival
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,741 mi
Madison, NC
72 mi away
Good Deal
$31,519
- 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:
- Automatic
- Mileage:
- 32,807
- Stock #:
- T9771A
- VIN:
- 1GCRYCEF1KZ321610
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
32,807 mi
Greensboro, NC
81 mi away
Good Deal
$33,199
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 63,185
- Stock #:
- A1077
- VIN:
- 3GCPDCEK7PG128692
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,185 mi
Franklin, VA
99 mi away
Good Deal
$35,294
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 46,365
- Stock #:
- P1208
- VIN:
- 1GCPYCEF9MZ293789
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,365 mi
Home delivery from Middlesboro, KY
Price includes $550 shipping
Good Deal
$36,149
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2,383
- Stock #:
- MT0270A
- VIN:
- 3GCPKCEK1TG342691
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,383 mi
Kernersville, NC
87 mi away
Great Deal
$44,799
$43,799
- 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:
- 52,310
- Stock #:
- DT9C00066B
- VIN:
- 3GCPDCEK1RG286951
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,310 mi
Wake Forest, NC
66 mi away
Fair Deal
$39,399
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,501
- Stock #:
- 7007182A
- VIN:
- 3GCPDCEK1NG607137
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,501 mi
Sanford, NC
91 mi away
Good Deal
$34,770
- 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:
- 30,724
- Stock #:
- 307401B
- VIN:
- 1GCPYCEF2MZ347210
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,724 mi
Kernersville, NC
86 mi away
Good Deal
$37,000
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 21,000
- Stock #:
- H7616A
- VIN:
- 3GCUKCE8XSG249254
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,000 mi
Martinsville, VA
64 mi away
Great Deal
$42,583
- 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 (Charcoal)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 135,132
- Stock #:
- 250850
- VIN:
- 1GCPYCEF4LZ250850
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
135,132 mi
Home delivery from Salt Lake City, UT
Price includes $2,694 shipping
Fair Deal
$24,594
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,319
- Stock #:
- 260883A
- VIN:
- 3GCPKCEK1TG191626
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,319 mi
Home delivery from Canfield, OH
Price includes $470 shipping
Great Deal
$42,868
$41,868
- 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
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $501 shipping
Great Deal
$29,401
- 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:
- 85,119
- Stock #:
- 181899
- VIN:
- 3GCPYCEF6LG181899
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,119 mi
South Boston, VA
12 mi away
Good Deal
$29,792
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,741
- Stock #:
- 363238A
- VIN:
- 1GCPYCEF1MZ393238
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,741 mi
Madison, NC
72 mi away
Good Deal
$31,519
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Mileage:
- 48,929
- Stock #:
- CJ28670A
- VIN:
- 3GCUDCED1RG130283
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,929 mi
Roanoke, VA
76 mi away
Good Deal
$41,699
- 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 Gji
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 87,242
- Stock #:
- CT12046B-3
- VIN:
- 1GCRYCEF3KZ184220
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
87,242 mi
Covington, VA
99 mi away
Fair Deal
$29,149
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,178
- Stock #:
- T1616
- VIN:
- 3GCPDCEK4PG172875
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,178 mi
Home delivery from Shelby, NC
Price includes $285 shipping
Fair Deal
$41,084
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 75,829
- Stock #:
- 29456
- VIN:
- 1GCPYCEF4LZ373368
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,829 mi
Home delivery from Cambridge, OH
Price includes $411 shipping
Good Deal
$30,188
- 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:
- Automatic
- Mileage:
- 80,389
- Stock #:
- 103642
- VIN:
- 3GCPDCEK6RG103642
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,389 mi
Home delivery from Mobile, AL
Price includes $1,380 shipping
Fair Deal
$35,575
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,612
- Stock #:
- 19575B
- VIN:
- 3GCPKCEK4SG354574
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,612 mi
Home delivery from Marietta, GA
Price includes $570 shipping
Great Deal
$42,637
- 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, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 114,493
- Stock #:
- 36967B
- VIN:
- 1GCPYCEF8MZ383953
Price drop
-$2,173
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
114,493 mi
High Point, NC
89 mi away
Fair Deal
$30,511
$28,338
- 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:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 17,739
- Stock #:
- T11707B
- VIN:
- 3GCUKCED3SG216576
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,739 mi
Cary, NC
70 mi away
Fair Deal
$47,303
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Red Oak, VA?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,761.35. The average price has decreased by -0.8% since last year. The 177 for sale near Red Oak, VA on CarGurus, range from $20,839 to $66,961 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Red Oak, VA have no reported accidents or damage?
147 out of 177 for sale near Red Oak, VA 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.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
Relevant articles
CarGurus Editorial Team
Best Truck Lease Deals in August 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
CarGurus Editorial Team
Car Deals with 0% APR in August 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
CarGurus Editorial Team
Best Car Deals in August 2026
In the market for a new or used car this year? Whether you’re looking to buy or lease, we’ve collated a list of the best car deals available this month.
Chevrolet Silverado 1500 LT in Red Oak VAChevrolet Silverado 1500 RST in Red Oak VAChevrolet Silverado 1500 LTZ in Red Oak VAChevrolet Silverado 1500 LT Trail Boss in Red Oak VAChevrolet Silverado 1500 LT1 in Red Oak VAChevrolet Silverado 1500 Custom in Red Oak VAChevrolet Silverado 1500 High Country in Red Oak VAChevrolet Silverado 1500 Custom Trail Boss in Red Oak VAChevrolet Silverado 1500 Work Truck in Red Oak VA
Chevrolet Silverado 1500 in Danville VAChevrolet Silverado 1500 in Lynchburg VAChevrolet Silverado 1500 in Raleigh NCChevrolet Silverado 1500 in Martinsville VAChevrolet Silverado 1500 in Rocky Mount NCChevrolet Silverado 1500 in Greensboro NCChevrolet Silverado 1500 in Roanoke VAChevrolet Silverado 1500 in Richmond VAChevrolet Silverado 1500 in Charlottesville VA
Chevrolet Silverado 1500 in Red Oak VAOld Chevy Trucks for Sale in Red Oak VAClassic Muscle Cars for Sale in Red Oak VAChevrolet Trucks For Sale in Red Oak VACheap Muscle Cars for Sale in Red Oak VAWork Trucks for Sale in Red Oak VAReliable Cars For Sale in Red Oak VAAmerican Made Trucks For Sale in Red Oak VABest Pickup Trucks For Sale in Red Oak VABest Cars Under $5,000 For Sale in Red Oak VA
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in Red OakUsed SUVs / Crossovers for Sale with Low Mileage in Red OakUsed Hatchbacks for Sale with Low Mileage in Red OakUsed Convertibles for Sale with Low Mileage in Red OakUsed Vans for Sale with Low Mileage in Red OakUsed Minivans for Sale with Low Mileage in Red OakUsed Pickup Trucks for Sale with Low Mileage in Red OakUsed Coupes for Sale with Low Mileage in Red OakUsed Wagons for Sale with Low Mileage in Red Oak
