Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearRoscoe, SD
100 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $2,148 shipping
Good Deal
$32,111
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Shadow Gray Metallic
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 63,610
- Stock #:
- 20402XXA
- VIN:
- 1GCPYCEKXNZ105540
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,610 mi
Home delivery from Glenwood, MN
Price includes $290 shipping
Good Deal
$31,630
- 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:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $995 shipping
Good Deal
$31,480
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 46,820
- Stock #:
- 16017
- VIN:
- 3GCPKCEKXSG328917
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,820 mi
Home delivery from Smithfield, NC
Price includes $2,586 shipping
Fair Deal
$40,685
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 105,556
- Stock #:
- C4134879AA
- VIN:
- 1GCPYCEFXLZ174700
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
105,556 mi
Home delivery from Ft Benton, MT
Price includes $704 shipping
Fair Deal
$28,453
- 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:
- Silver
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 64,044
- Stock #:
- 290751
- VIN:
- 1GCPYCEL5MZ290751
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
64,044 mi
Home delivery from Gallup, NM
Price includes $1,262 shipping
Good Deal
$33,756
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,213
- Stock #:
- 153965B
- VIN:
- 1GCPYCEF5MZ153965
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,213 mi
Home delivery from Dallas, TX
Price includes $882 shipping
Fair Deal
$31,607
- 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)
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 71,652
- Stock #:
- A88197
- VIN:
- 1GCPYCEF1MZ270913
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,652 mi
Home delivery from Herculaneum, MO
Price includes $1,348 shipping
Fair Deal
$33,924
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 73,176
- Stock #:
- 2535
- VIN:
- 1GCPYCEF5KZ368419
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
73,176 mi
Home delivery from Milton, WI
Price includes $546 shipping
Fair Deal
$31,034
- 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 $1,317 shipping
Great Deal
$29,760
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 37,517
- Stock #:
- 117339
- VIN:
- 3GCPDCEK2PG117339
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
37,517 mi
Home delivery from Placentia, CA
Price includes $1,893 shipping
Fair Deal
$38,616
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 155,893
- Stock #:
- 14093
- VIN:
- 1GCPYCEF8MZ147433
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
155,893 mi
Home delivery from Rogers, MN
Price includes $560 shipping
Good Deal
$22,409
- 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:
- 111,601
- Stock #:
- 330935P
- VIN:
- 1GCPYCEF5MZ330935
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
111,601 mi
Home delivery from Alexandria, MN
Price includes $290 shipping
Fair Deal
$27,416
- 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:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $1,059 shipping
Fair Deal
$36,549
- 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 $792 shipping
Great Deal
$29,692
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 104,499
- Stock #:
- 14237
- VIN:
- 1GCPYCEF8MZ381894
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,499 mi
Home delivery from Rogers, MN
Price includes $560 shipping
Fair Deal
$28,609
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 57,809
- Stock #:
- MX5448
- VIN:
- 1GCPYCEF7MZ420099
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,809 mi
Home delivery from Michigan Center, MI
Price includes $1,400 shipping
Good Deal
$33,423
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 78,192
- Stock #:
- WD115203
- VIN:
- 1GCPYCEK9NZ115203
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
78,192 mi
Home delivery from Wadena, MN
Price includes $213 shipping
Fair Deal
$30,561
- 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:
- Silver
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 89,677
- Stock #:
- M22974
- VIN:
- 1GCPYCEF3MZ327659
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,677 mi
Home delivery from Lehi, UT
Price includes $1,083 shipping
Good Deal
$29,676
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 58,589
- Stock #:
- 136006A
- VIN:
- 3GCUDCED9PG136006
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,589 mi
Home delivery from Alexandria, MN
Price includes $290 shipping
Fair Deal
$38,944
- 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:
- 13,956
- Stock #:
- 113812
- VIN:
- 3GCUDCED5RG113812
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,956 mi
Home delivery from Irving, TX
Price includes $1,754 shipping
Good Deal
$45,655
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 43,435
- Stock #:
- C1459
- VIN:
- 1GCRYCEF3KZ276170
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
43,435 mi
Home delivery from Burnsville, MN
Price includes $372 shipping
Fair Deal
$30,700
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 71,570
- Stock #:
- 261563A
- VIN:
- 3GCPYCEF7LG413605
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,570 mi
Home delivery from Glenwood, MN
Price includes $290 shipping
Good Deal
$31,130
- 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
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
135,132 mi
Home delivery from Salt Lake City, UT
Price includes $1,068 shipping
Good Deal
$22,968
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Roscoe, SD?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,290.88. The average price has decreased by -3.4% since last year. The 100 for sale near Roscoe, SD on CarGurus, range from $21,945 to $64,230 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Roscoe, SD have no reported accidents or damage?
89 out of 100 for sale near Roscoe, SD 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/MPGe.
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 Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Roscoe SDChevrolet Silverado 1500 RST in Roscoe SDChevrolet Silverado 1500 LTZ in Roscoe SDChevrolet Silverado 1500 LT Trail Boss in Roscoe SDChevrolet Silverado 1500 LT1 in Roscoe SDChevrolet Silverado 1500 Custom in Roscoe SDChevrolet Silverado 1500 High Country in Roscoe SDChevrolet Silverado 1500 Custom Trail Boss in Roscoe SDChevrolet Silverado 1500 Work Truck in Roscoe SD
Chevrolet Silverado 1500 in Jamestown NDChevrolet Silverado 1500 in Bismarck NDChevrolet Silverado 1500 in Fargo NDChevrolet Silverado 1500 in Cross State SDChevrolet Silverado 1500 in Sioux Falls SDChevrolet Silverado 1500 in Grand Forks NDChevrolet Silverado 1500 in Minot NDChevrolet Silverado 1500 in Rapid City SDChevrolet Silverado 1500 in Saint Cloud MN
Chevrolet Silverado 1500 in Roscoe SDOld Chevy Trucks for Sale in Roscoe SDClassic Muscle Cars for Sale in Roscoe SDChevrolet Trucks For Sale in Roscoe SDCheap Muscle Cars for Sale in Roscoe SDWork Trucks for Sale in Roscoe SDReliable Cars For Sale in Roscoe SDAmerican Made Trucks For Sale in Roscoe SDBest Pickup Trucks For Sale in Roscoe SDBest Cars Under $5,000 For Sale in Roscoe SD
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 RoscoeUsed SUVs / Crossovers for Sale with Low Mileage in RoscoeUsed Hatchbacks for Sale with Low Mileage in RoscoeUsed Convertibles for Sale with Low Mileage in RoscoeUsed Vans for Sale with Low Mileage in RoscoeUsed Minivans for Sale with Low Mileage in RoscoeUsed Pickup Trucks for Sale with Low Mileage in RoscoeUsed Coupes for Sale with Low Mileage in RoscoeUsed Wagons for Sale with Low Mileage in Roscoe
