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 Waunakee, WI

153 results
Waunakee, WI
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Al Piemonte Chevrolet of Dundee

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 miles

$37,850

Fair Deal
East Dundee, IL
98 mi away
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:
45,678
Stock number:
K8591
VIN:
3GCUDCED1PG323353

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,732 miles

$29,655

Good Deal
Milwaukee, WI
78 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:
85,732
Stock number:
UJ671
VIN:
1GCPYCEF5MZ273765

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,392 miles

$27,055

Fair Deal
Janesville, WI
42 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:
114,392
Stock number:
W251000B
VIN:
3GCPYCEF8LG172685

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,098 miles

$29,397

Good Deal
Mchenry, IL
84 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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
65,098
Stock number:
MSK230
VIN:
3GCPYCEF8KG158817

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,172 miles

$41,229

Great Deal
Plymouth, WI
85 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

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,320 miles

$37,667

Good Deal
Rochelle, IL
89 mi away
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:
8-Speed Automatic
Mileage:
32,320
Stock number:
G1333A
VIN:
3GCPDCEK9PG187453

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,035 miles

$26,985

Fair Deal
Sparta, WI
85 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

85,732 miles

$29,655

Good Deal
Milwaukee, WI
78 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:
85,732
Stock number:
UJ671
VIN:
1GCPYCEF5MZ273765

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,430 miles

$33,555

Fair Deal
Beloit, WI
52 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 (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
63,430
Stock number:
P2472
VIN:
1GCPYCEF7MZ371101

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,752 miles

$40,681

Fair Deal
Sterling, IL
96 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
20,752
Stock number:
P3275
VIN:
3GCPDCEK9RG217862

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,064 miles

$44,786

Good Deal
West Bend, WI
65 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

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

51,071 miles

$30,000

Fair Deal
Mchenry, IL
85 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,071
Stock number:
UT20663
VIN:
1GCRYCEF4KZ312867

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,115 miles

$33,599

Good Deal
Franklin, WI
74 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:
55,115
Stock number:
V7479
VIN:
3GCPYCEFXMG303472

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,058 miles

$38,735

Good Deal
Certified Pre-Owned
Slinger, WI
61 mi away
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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
46,058
Stock number:
S3051
VIN:
3GCUDCED7PG215173

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,064 miles

$44,786

Good Deal
West Bend, WI
65 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. / Waunakee
  • Chevrolet Silverado 1500 LT in Waunakee WI

  • Chevrolet Silverado 1500 RST in Waunakee WI

  • Chevrolet Silverado 1500 LTZ in Waunakee WI

  • Chevrolet Silverado 1500 LT Trail Boss in Waunakee WI

  • Chevrolet Silverado 1500 LT1 in Waunakee WI

  • Chevrolet Silverado 1500 Custom in Waunakee WI

  • Chevrolet Silverado 1500 High Country in Waunakee WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Waunakee WI

  • Chevrolet Silverado 1500 Work Truck in Waunakee WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Dubuque IA

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in La Crosse WI

  • Chevrolet Silverado 1500 in Waunakee WI

  • Old Chevy Trucks for Sale in Waunakee WI

  • Classic Muscle Cars for Sale in Waunakee WI

  • Chevrolet Trucks For Sale in Waunakee WI

  • Cheap Muscle Cars for Sale in Waunakee WI

  • Work Trucks for Sale in Waunakee WI

  • Reliable Cars For Sale in Waunakee WI

  • American Made Trucks For Sale in Waunakee WI

  • Best Pickup Trucks For Sale in Waunakee WI

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Waunakee 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

  • Kayser Chevrolet Buick GMC

  • Kayser Chevrolet Sauk City

  • Don Larson Superstore

  • Hallada Auto Group

  • Brodhead Automobiles

  • Symdon Chevrolet

  • Napleton Chevrolet Columbus

  • Homan Chevrolet Buick

  • Bergstrom Chevrolet of Madison

  • Bergstrom Chevrolet of Middleton

  • Zimbrick Chevrolet

  • Burtness Chevrolet

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

© 2025 CarGurus, Inc., All Rights Reserved.