CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Friendship, WI

132 results
Friendship, WI
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Jon Green Family Auto

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,076 miles

$32,779

Fair Deal
Milton, WI
94 mi away
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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
67,076
Stock number:
1909
VIN:
1GCPYCEF2MZ181593

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

97,438 miles

$27,491

Good Deal
Fond du Lac, WI
68 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
97,438
Stock number:
DB34500
VIN:
1GCPYCEF8LZ119582

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,528 miles

$26,512

Good Deal
Madison, WI
66 mi away
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
108,528
Stock number:
J4899A
VIN:
1GCPYCEF3LZ143028

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,793 miles

$31,933

Great Deal
Wausau, WI
65 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Cherry Red
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
45,793
Stock number:
E10623
VIN:
1GCPYCEK9NZ138657

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,981 miles

$31,658

Fair Deal
Green Bay, WI
93 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray
Interior color:
Black
Transmission:
Automatic
Mileage:
68,981
Stock number:
F254966A
VIN:
1GCPYCEK8NZ133000

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,035 miles

$26,481

Fair Deal
Sparta, WI
51 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
83,035
Stock number:
KZ258374
VIN:
1GCRYCEF6KZ258374

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,450 miles

$28,253

Good Deal
Waukon, IA
98 mi away
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 Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,450
Stock number:
17669
VIN:
1GCPYCEF5MZ285561

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,076 miles

$32,779

Fair Deal
Milton, WI
94 mi away
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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
67,076
Stock number:
1909
VIN:
1GCPYCEF2MZ181593

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

121,739 miles

$25,990

Fair Deal
Sun Prairie, WI
62 mi away
Year:
2021
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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
121,739
Stock number:
71590
VIN:
1GCPYCEH5MZ318592

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,978 miles

$38,993

Good Deal
Certified Pre-Owned
Appleton, WI
68 mi away
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:
Automatic
Mileage:
26,978
Stock number:
254976C
VIN:
3GCPDCEK0RG385356

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,172 miles

$41,229

Good Deal
Plymouth, WI
93 mi away
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 (gba)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black (h0u)
Transmission:
Automatic
Mileage:
18,172
Stock number:
9753
VIN:
3GCUDCED9RG306982

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,096 miles

$34,393

Fair Deal
Wausau, WI
65 mi away
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:
56,096
Stock number:
C0255A
VIN:
1GCPYCEF4MZ163273

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,064 miles

$44,317

Good Deal
West Bend, WI
87 mi away
Year:
2024
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:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
4,064
Stock number:
T68060A
VIN:
3GCUDCE82RG103161

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Wisconsin
  6. / Friendship

  • Chevrolet Silverado 1500 LT in Friendship WI

  • Chevrolet Silverado 1500 RST in Friendship WI

  • Chevrolet Silverado 1500 LTZ in Friendship WI

  • Chevrolet Silverado 1500 LT Trail Boss in Friendship WI

  • Chevrolet Silverado 1500 LT1 in Friendship WI

  • Chevrolet Silverado 1500 Custom in Friendship WI

  • Chevrolet Silverado 1500 High Country in Friendship WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Friendship WI

  • Chevrolet Silverado 1500 Work Truck in Friendship WI

  • Chevrolet Silverado 1500 in Marshfield WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in La Crosse WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Green Bay WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Eau Claire WI

  • Chevrolet Silverado 1500 in Dubuque IA

  • Chevrolet Silverado 1500 in Friendship WI

  • Old Chevy Trucks for Sale in Friendship WI

  • Classic Muscle Cars for Sale in Friendship WI

  • Chevrolet Trucks For Sale in Friendship WI

  • Cheap Muscle Cars for Sale in Friendship WI

  • Work Trucks for Sale in Friendship WI

  • Reliable Cars For Sale in Friendship WI

  • American Made Trucks For Sale in Friendship WI

  • Best Pickup Trucks For Sale in Friendship WI

  • Best Cars Under $5,000 For Sale in Friendship WI

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Friendship WI

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Don Larson Superstore

  • Kayser Chevrolet Sauk City

  • Kudick Chevrolet

  • Homan Chevrolet GMC of Ripon

  • Len Dudas Motors

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.