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 LT Trail Boss for Sale near Baraboo, WI

325 results
Baraboo, WI
2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD INFINITI Milwaukee

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

73,662 miles

$34,412

Good Deal
West Allis, WI
92 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
73,662
Stock number:
PM4258
VIN:
1GCPYFED0MZ205115

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,361 miles

$37,977

Fair Deal
Certified Pre-Owned
Milwaukee, WI
97 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,361
Stock number:
C19605NC
VIN:
1GCPYFED0LZ297695

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,397 miles

$38,957

Great Deal
Evansville, WI
54 mi away
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:
Cherry Red
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,397
Stock number:
262091
VIN:
3GCPYFED4NG196341

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,361 miles

$37,977

Fair Deal
Certified Pre-Owned
Milwaukee, WI
97 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,361
Stock number:
C19605NC
VIN:
1GCPYFED0LZ297695

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

79,496 miles

$33,990

Fair Deal
Weyauwega, WI
71 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
79,496
Stock number:
RA1773
VIN:
3GCPYFED5MG438763

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,115 miles

$46,918

Good Deal
Certified Pre-Owned
Cedarburg, WI
89 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,115
Stock number:
26131A
VIN:
3GCUDFEL4NG505103

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,397 miles

$38,957

Great Deal
Evansville, WI
54 mi away
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:
Cherry Red
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,397
Stock number:
262091
VIN:
3GCPYFED4NG196341

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

49,803 miles

$41,899

Good Deal
Plymouth, WI
93 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
49,803
Stock number:
A114069T
VIN:
3GCUDFET6NG545778

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,676 miles

$34,979

Good Deal
Milton, WI
64 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:
Northsky Blue
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
59,676
Stock number:
1928
VIN:
1GCPYFED1LZ286169

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

117,746 miles

$28,093

Good Deal
Plymouth, WI
92 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 (gba)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Gideon/Very Dark Atmosphere (hvc)
Transmission:
8-Speed Automatic
Mileage:
117,746
Stock number:
G4583A
VIN:
1GCPYFED9KZ149088

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,585 miles

$34,998

Good Deal
Certified Pre-Owned
Harvard, IL
92 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
65,585
Stock number:
25242A
VIN:
1GCPYFEDXMZ105359

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,065 miles

$31,000

Great Deal
Neenah, WI
81 mi away
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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
JET BLACK
Transmission:
Automatic
Mileage:
96,065
Stock number:
D41638
VIN:
3GCPYFED3NG114552

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

113,576 miles

$30,999

Fair Deal
Saukville, WI
92 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:
113,576
Stock number:
24697A
VIN:
3GCPYFEL5NG119677

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

40,506 miles

$38,882

Great Deal
Lake Geneva, WI
91 mi away
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:
Cherry Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,506
Stock number:
30T1419A
VIN:
1GCPYFEL0MZ419075

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,848 miles

$39,989

Great Deal
Johnson Creek, WI
55 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Red Hot
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,848
Stock number:
9350
VIN:
3GCUDFET3NG544958

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,380 miles

$34,945

Fair Deal
Orfordville, WI
63 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
78,380
Stock number:
P7559A
VIN:
1GCPYFEL4LZ379680

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,520 miles

$40,897

Good Deal
Store transfer to Madison, WI
1,610 mi away • Price includes $1,899 shipping Price includes $1,899 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Blue
Interior color:
Black
Transmission:
Automatic
Mileage:
19,520
Stock number:
26433898
VIN:
1GCPYFEL0NZ228094

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

8,642 miles

$52,988

Good Deal
Plymouth, WI
92 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:
Black
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
8,642
Stock number:
9641
VIN:
3GCUDFE89RG340764

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

48,696 miles

$37,593

Fair Deal
Janesville, WI
64 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:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
48,696
Stock number:
P30255
VIN:
1GCPYFED8LZ131201

Sponsored

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

  • Chevrolet Silverado 1500 LT in Baraboo WI

  • Chevrolet Silverado 1500 RST in Baraboo WI

  • Chevrolet Silverado 1500 LTZ in Baraboo WI

  • Chevrolet Silverado 1500 LT Trail Boss in Baraboo WI

  • Chevrolet Silverado 1500 LT1 in Baraboo WI

  • Chevrolet Silverado 1500 Custom in Baraboo WI

  • Chevrolet Silverado 1500 High Country in Baraboo WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Baraboo WI

  • Chevrolet Silverado 1500 Work Truck in Baraboo 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 La Crosse WI

  • Chevrolet Silverado 1500 in Dubuque IA

  • Chevrolet Silverado 1500 in Marshfield WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Baraboo WI

  • Old Chevy Trucks for Sale in Baraboo WI

  • Classic Muscle Cars for Sale in Baraboo WI

  • Chevrolet Trucks For Sale in Baraboo WI

  • Cheap Muscle Cars for Sale in Baraboo WI

  • Work Trucks for Sale in Baraboo WI

  • Reliable Cars For Sale in Baraboo WI

  • American Made Trucks For Sale in Baraboo WI

  • Best Pickup Trucks For Sale in Baraboo WI

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Baraboo 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 Sauk City

  • Don Larson Superstore

  • Hallada Auto Group

  • Napleton Chevrolet Columbus

  • Kudick Chevrolet

  • Bergstrom Chevrolet of Madison

  • Bergstrom Chevrolet of Middleton

  • Zimbrick 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

© 2026 CarGurus, Inc., All Rights Reserved.