Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearChatham, VA
200 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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
New arrival
Sponsored by Parks Chevrolet Kernersville
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,724 mi
Kernersville, NC
61 mi away
Good Deal
$37,500
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,738
- Stock #:
- N26570B
- VIN:
- 3GCUDCED6RG304963
New arrival
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,738 mi
Fuquay Varina, NC
93 mi away
Good Deal
$43,281
- 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:
- Automatic
- Mileage:
- 38,250
- Stock #:
- ZT11189A
- VIN:
- 3GCPDCEK4RG286281
New arrival
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
38,250 mi
Cary, NC
83 mi away
Fair Deal
$40,798
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,506
- Stock #:
- P1822
- VIN:
- 3GCPKCEK0SG333141
Price drop
-$1,000
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,506 mi
Home delivery from Brodheadsville, PA
Price includes $712 shipping
Good Deal
$45,200
$44,200
- 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:
- 56,969
- Stock #:
- 3927
- VIN:
- 1GCRYCEF9KZ249670
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Home delivery from Belford, NJ
Price includes $595 shipping
Good Deal
$30,268
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 33,975
- Stock #:
- BCP49230
- VIN:
- 3GCUDCED3RG410576
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,975 mi
Bedford, VA
34 mi away
Great Deal
$40,767
- 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
28 mi away
Great Deal
$42,583
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 103,407
- Stock #:
- 11653
- VIN:
- 3GCPYCEF6KG188558
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
103,407 mi
Pittsboro, NC
78 mi away
Great Deal
$25,877
- 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 $474 shipping
Good Deal
$36,073
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,114
- Stock #:
- G26441A
- VIN:
- 3GCUDCED6RG140842
Price drop
-$2,292
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,114 mi
Home delivery from Bartonsville, PA
Price includes $549 shipping
Good Deal
$42,341
$40,049
- 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
94 mi away
Good Deal
$34,770
- 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:
- 32,064
- Stock #:
- DT9C95226A
- VIN:
- 3GCPDCEK9RG249131
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,064 mi
Wake Forest, NC
85 mi away
Good Deal
$39,499
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 127,301
- Stock #:
- D355737
- VIN:
- 3GCPYCEF7LG355737
Price drop
-$510
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
127,301 mi
Raleigh, NC
91 mi away
Fair Deal
$24,999
$24,489
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $524 shipping
Great Deal
$31,479
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 69,041
- Stock #:
- K26986A
- VIN:
- 1GCRYCEF8KZ326786
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
69,041 mi
Home delivery from Ashland, KY
Price includes $624 shipping
Good Deal
$29,907
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 22,873
- Stock #:
- 402210
- VIN:
- 3GCPDCEK4RG402210
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,873 mi
Home delivery from Orlando, FL
Price includes $583 shipping
Fair Deal
$42,970
- 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
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,383 mi
Kernersville, NC
62 mi away
Good Deal
$44,799
- 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
- Transmission:
- Automatic
- Mileage:
- 21,670
- Stock #:
- F22566B
- VIN:
- 3GCUKCED2SG203429
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,670 mi
Home delivery from Parkersburg, WV
Price includes $303 shipping
Fair Deal
$45,845
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 115,088
- Stock #:
- 144370
- VIN:
- 1GCPYCEF5KZ345870
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
115,088 mi
Home delivery from Fredericksburg, VA
Price includes $225 shipping
Fair Deal
$28,121
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red
- Fuel type:
- Diesel
- Interior color:
- Black
- Mileage:
- 110,590
- Stock #:
- 301317
- VIN:
- 3GCUDCE84PG301317
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $1,556 shipping
Great Deal
$30,776
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 87,128
- Stock #:
- A1219
- VIN:
- 1GCPYCEF4MZ250624
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
87,128 mi
Home delivery from Chattanooga, TN
Price includes $684 shipping
Fair Deal
$32,462
- 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
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,724 mi
Kernersville, NC
61 mi away
Good Deal
$37,500
- 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:
- 12,609
- Stock #:
- 19575B
- VIN:
- 3GCPKCEK4SG354574
Price drop
-$1,000
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,609 mi
Home delivery from Marietta, GA
Price includes $525 shipping
Good Deal
$44,312
$43,312
- 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:
- 15,688
- Stock #:
- 365209
- VIN:
- 3GCPDCEK1PG365209
New arrival
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,688 mi
Covington, VA
71 mi away
Fair Deal
$43,349
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Chatham, VA?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,838.96. The average price has decreased by -0.7% since last year. The 184 for sale near Chatham, VA on CarGurus, range from $21,984 to $68,087 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Chatham, VA have no reported accidents or damage?
166 out of 184 for sale near Chatham, 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.
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 Chatham VAChevrolet Silverado 1500 RST in Chatham VAChevrolet Silverado 1500 LTZ in Chatham VAChevrolet Silverado 1500 LT Trail Boss in Chatham VAChevrolet Silverado 1500 LT1 in Chatham VAChevrolet Silverado 1500 Custom in Chatham VAChevrolet Silverado 1500 High Country in Chatham VAChevrolet Silverado 1500 Custom Trail Boss in Chatham VAChevrolet Silverado 1500 Work Truck in Chatham VA
Chevrolet Silverado 1500 in Danville VAChevrolet Silverado 1500 in Martinsville VAChevrolet Silverado 1500 in Lynchburg VAChevrolet Silverado 1500 in Roanoke VAChevrolet Silverado 1500 in Greensboro NCChevrolet Silverado 1500 in Blacksburg VAChevrolet Silverado 1500 in Winston Salem NCChevrolet Silverado 1500 in Raleigh NCChevrolet Silverado 1500 in Charlottesville VA
Chevrolet Silverado 1500 in Chatham VAOld Chevy Trucks for Sale in Chatham VAClassic Muscle Cars for Sale in Chatham VAChevrolet Trucks For Sale in Chatham VACheap Muscle Cars for Sale in Chatham VAWork Trucks for Sale in Chatham VAReliable Cars For Sale in Chatham VAAmerican Made Trucks For Sale in Chatham VABest Pickup Trucks For Sale in Chatham VABest Cars Under $5,000 For Sale in Chatham 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 ChathamUsed SUVs / Crossovers for Sale with Low Mileage in ChathamUsed Hatchbacks for Sale with Low Mileage in ChathamUsed Convertibles for Sale with Low Mileage in ChathamUsed Vans for Sale with Low Mileage in ChathamUsed Minivans for Sale with Low Mileage in ChathamUsed Pickup Trucks for Sale with Low Mileage in ChathamUsed Coupes for Sale with Low Mileage in ChathamUsed Wagons for Sale with Low Mileage in Chatham
