Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearFennimore, WI
149 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- 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:
- 3,034
- Stock #:
- U6026
- VIN:
- 3GCUKCED4TG147446
Sponsored by Vern Laures Chevrolet
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
3,034 mi
New Hampton, IA
86 mi away
Fair Deal
$48,614
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 9,296
- Stock #:
- C35845
- VIN:
- 3GCUDCED8RG199987
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
9,296 mi
Cedar Rapids, IA
85 mi away
Good Deal
$43,678
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 15,837
- Stock #:
- U6025
- VIN:
- 3GCUKCED6SG362213
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,837 mi
New Hampton, IA
86 mi away
Fair Deal
$45,614
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 78,807
- Stock #:
- 08P893
- VIN:
- 3GCPDCED8NG570945
Price drop
-$1,393
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
78,807 mi
Morrison, IL
87 mi away
Fair Deal
$33,904
$32,511
- 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:
- CYPRESS GRAY
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 11,352
- Stock #:
- 277668A
- VIN:
- 3GCPKCEK7SG347277
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,352 mi
Madison, WI
62 mi away
Fair Deal
$42,378
- 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:
- Shadow Gray Metallic (gji)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black (h1t)
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 96,517
- Stock #:
- 60391A
- VIN:
- 1GCPYCEH9KZ263965
Price drop
-$1,026
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
96,517 mi
Mount Horeb, WI
47 mi away
Great Deal
$25,216
$24,190
- 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:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $1,227 shipping
Good Deal
$33,043
- 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:
- 97,295
- Stock #:
- CT315C
- VIN:
- 1GCPYCEF3LZ126276
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
97,295 mi
Dyersville, IA
43 mi away
Good Deal
$26,791
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,288
- Stock #:
- B836
- VIN:
- 3GCPDCEK1RG221310
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,288 mi
Baraboo, WI
55 mi away
Good Deal
$37,135
- Year:
- 2023
- 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:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 59,654
- Stock #:
- 26F55B
- VIN:
- 3GCUDCE87PG294329
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,654 mi
Lake Mills, WI
87 mi away
Good Deal
$35,551
- 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:
- 44,728
- Stock #:
- C7738A
- VIN:
- 3GCPYCEF2MG122513
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
44,728 mi
Sauk City, WI
49 mi away
Fair Deal
$35,697
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 157,898
- VIN:
- 1GCRYCEF4KZ345075
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
157,898 mi
Portage, WI
70 mi away
Fair Deal
$19,264
- 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 (gba)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black (h1t)
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 111,354
- Stock #:
- 60166B
- VIN:
- 1GCRYCEF5KZ302364
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
111,354 mi
Mount Horeb, WI
47 mi away
Good Deal
$23,159
- 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:
- 39,868
- Stock #:
- 28210392
- VIN:
- 3GCPDCEK2PG188511
New arrival
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,868 mi
Store transfer to Madison, WI
Price includes $649 shipping
Good Deal
$36,647
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,048 shipping
Fair Deal
$33,011
- 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 $861 shipping
Fair Deal
$31,236
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 34,417
- Stock #:
- 5706A
- VIN:
- 3GCUDCED0PG304292
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,417 mi
Waverly, IA
96 mi away
Good Deal
$39,833
- 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:
- GRY
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 62,918
- Stock #:
- 11258
- VIN:
- 3GCPDCED1NG673222
Price drop
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,918 mi
Home delivery from Blackwood, NJ
Price includes $836 shipping
Good Deal
$34,618
$33,618
- 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 $1,319 shipping
Good Deal
$34,809
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,249
- Stock #:
- GM31867T
- VIN:
- 1GCPYCEF6MZ370442
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,249 mi
Home delivery from Gurnee, IL
Price includes $286 shipping
Great Deal
$25,662
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 55,859
- Stock #:
- F1344A
- VIN:
- 3GCPYCEL1NG100154
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,859 mi
Home delivery from Barrington, IL
Price includes $1,390 shipping
Fair Deal
$35,661
- 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 Hot G7c
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black H1t
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 46,558
- Stock #:
- PHN1330A
- VIN:
- 1GCPYCEF0MZ243928
Price drop
-$1,005
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,558 mi
Home delivery from Park Hills, MO
Price includes $1,071 shipping
Fair Deal
$35,837
$34,832
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,382
- Stock #:
- C16133A
- VIN:
- 3GCPYCEK7NG140231
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,382 mi
Home delivery from North Pekin, IL
Price includes $177 shipping
Good Deal
$32,050
- 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:
- 32,899
- Stock #:
- C261721A
- VIN:
- 3GCUDCED4RG116295
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,899 mi
Cedar Rapids, IA
85 mi away
Fair Deal
$42,895
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Fennimore, WI?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,096.69. The average price has decreased by -4.5% since last year. The 134 for sale near Fennimore, WI on CarGurus, range from $19,440 to $62,439 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Fennimore, WI have no reported accidents or damage?
110 out of 134 for sale near Fennimore, WI 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
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
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.
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 Fennimore WIChevrolet Silverado 1500 RST in Fennimore WIChevrolet Silverado 1500 LTZ in Fennimore WIChevrolet Silverado 1500 LT Trail Boss in Fennimore WIChevrolet Silverado 1500 LT1 in Fennimore WIChevrolet Silverado 1500 Custom in Fennimore WIChevrolet Silverado 1500 High Country in Fennimore WIChevrolet Silverado 1500 Custom Trail Boss in Fennimore WIChevrolet Silverado 1500 Work Truck in Fennimore WI
Chevrolet Silverado 1500 in Dubuque IAChevrolet Silverado 1500 in Madison WIChevrolet Silverado 1500 in La Crosse WIChevrolet Silverado 1500 in Clinton IAChevrolet Silverado 1500 in Janesville WIChevrolet Silverado 1500 in Cedar Rapids IAChevrolet Silverado 1500 in Waterloo IAChevrolet Silverado 1500 in Rockford ILChevrolet Silverado 1500 in Davenport IA
Chevrolet Silverado 1500 in Fennimore WIOld Chevy Trucks for Sale in Fennimore WIClassic Muscle Cars for Sale in Fennimore WIChevrolet Trucks For Sale in Fennimore WICheap Muscle Cars for Sale in Fennimore WIWork Trucks for Sale in Fennimore WIReliable Cars For Sale in Fennimore WIAmerican Made Trucks For Sale in Fennimore WIBest Pickup Trucks For Sale in Fennimore WIBest Cars Under $5,000 For Sale in Fennimore WI
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 FennimoreUsed SUVs / Crossovers for Sale with Low Mileage in FennimoreUsed Hatchbacks for Sale with Low Mileage in FennimoreUsed Convertibles for Sale with Low Mileage in FennimoreUsed Vans for Sale with Low Mileage in FennimoreUsed Minivans for Sale with Low Mileage in FennimoreUsed Pickup Trucks for Sale with Low Mileage in FennimoreUsed Coupes for Sale with Low Mileage in FennimoreUsed Wagons for Sale with Low Mileage in Fennimore
