CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
  • Sell
    • Sell my car
    • Car values
  • Research
    • Test drive reviews
    • Price trends
    • Compare cars
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Winnipeg, MB

23 results
Winnipeg, MB
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD McNaught Buick GMC

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

122,153 kilometres

$39,300

Fair Deal
Winnipeg, MB
10 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
122,153
Stock number:
724951
VIN:
3GCPDCED7NG590927

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,295 kilometres

$49,298

Great Deal
Winnipeg, MB
5 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
21,295
Stock number:
P11164
VIN:
3GCUDCED2RG209588

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

162,350 kilometres

$35,999

Good Deal
East Selkirk, MB
27 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Interior colour:
Black
Transmission:
Automatic
Mileage:
162,350
Stock number:
255628
VIN:
3GCPYCEK1NG195620

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,295 kilometres

$49,298

Great Deal
Winnipeg, MB
5 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
21,295
Stock number:
P11164
VIN:
3GCUDCED2RG209588

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

162,350 kilometres

$35,999

Good Deal
East Selkirk, MB
27 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Interior colour:
Black
Transmission:
Automatic
Mileage:
162,350
Stock number:
255628
VIN:
3GCPYCEK1NG195620

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,112 kilometres

$44,999

Fair Deal
Certified Pre-Owned
Winnipeg, MB
5 km 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 colour:
Sand Dune Metallic
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
76,112
Stock number:
T250832A
VIN:
3GCPDCED3NG667177

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

122,153 kilometres

$39,300

Fair Deal
Winnipeg, MB
10 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
122,153
Stock number:
724951
VIN:
3GCPDCED7NG590927

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

122,141 kilometres

$39,698

High Price
Winnipeg, MB
8 km 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 colour:
Black
Combined gas mileage:
16 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
122,141
Stock number:
AB4428B
VIN:
1GCPYCEF5MZ416844

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

228,629 kilometres

$29,995

High Price
Headingley, MB
19 km away
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 colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
228,629
Stock number:
P1537
VIN:
3GCPDCEK3NG653729

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

  • Chevrolet Silverado 1500 LT in Winnipeg MB

  • Chevrolet Silverado 1500 RST in Winnipeg MB

  • Chevrolet Silverado 1500 LT Trail Boss in Winnipeg MB

  • Chevrolet Silverado 1500 Custom in Winnipeg MB

  • Chevrolet Silverado 1500 High Country in Winnipeg MB

  • Chevrolet Silverado 1500 Custom Trail Boss in Winnipeg MB

  • Chevrolet Silverado 1500 LTZ in Winnipeg MB

  • Chevrolet Silverado 1500 Work Truck in Winnipeg MB

  • Chevrolet Silverado 1500 LS in Winnipeg MB

  • Chevrolet Silverado 1500 in Brandon MB

  • Chevrolet Silverado 1500 in Regina SK

  • Chevrolet Silverado 1500 in Thunder Bay ON

  • Chevrolet Silverado 1500 in Moose Jaw SK

  • Chevrolet Silverado 1500 in Prince Albert SK

  • Chevrolet Silverado 1500 in Saskatoon SK

  • Chevrolet Silverado 1500 in Lloydminster SK

  • Chevrolet Silverado 1500 in Medicine Hat AB

  • Chevrolet Silverado 1500 in Sault Ste. Marie ON

  • Chevrolet Silverado 1500 in Winnipeg MB

  • Best Work Trucks for Sale in Winnipeg MB

  • Chevrolet Trucks For Sale in Winnipeg MB

  • Chevy Duramax Diesel Trucks for Sale in Winnipeg MB

  • Chevrolet SUVs & Crossovers for Sale in Winnipeg MB

  • Cheap Muscle Cars for Sale in Winnipeg MB

  • Chevrolet Silverado 1500 in Alberta

  • Chevrolet Silverado 1500 in British Columbia

  • Chevrolet Silverado 1500 in Manitoba

  • Chevrolet Silverado 1500 in New Brunswick

  • Chevrolet Silverado 1500 in Newfoundland and Labrador

  • Chevrolet Silverado 1500 in Northwest Territories

  • Chevrolet Silverado 1500 in Nova Scotia

  • Chevrolet Silverado 1500 in Nunavut

  • Chevrolet Silverado 1500 in Ontario

  • Chevrolet Silverado 1500 in Prince Edward Island

  • Chevrolet Silverado 1500 in Quebec

  • Chevrolet Silverado 1500 in Saskatchewan

  • Chevrolet Silverado 1500 in Yukon

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Winnipeg MB

  • All Used Cars

  • Cheap Cars

  • Manual Transmission Cars

  • Sports Cars

  • Hybrid Cars

  • Red Interior Cars

  • Electric Cars

  • Small Cars

  • AWD Cars

  • Cheap Automatic Transmission Cars

  • Classic Trucks

  • Conversion Vans

  • Three Quarter Ton Trucks

  • Diesel Trucks

  • Small Trucks

  • Chevrolet Diesel Trucks

  • Manual Diesel Trucks

  • One Ton Trucks

  • Cheap Trucks

  • Ford Trucks

  • Cheap SUVs

  • Mercedes-Benz Convertibles

  • Ford Diesel Trucks

  • Mercedes-Benz SUVs

  • BMW Convertibles

  • Chevrolet SUVs

  • Toyota SUVs

  • Nissan SUVs

  • Used Cars Under $10,000

  • Used Cars Under $5,000

  • 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

  • Birchwood Chevrolet Buick GMC

  • Jim Gauthier Chevrolet

  • Selkirk Chevrolet Buick GMC

  • Ledingham Chevrolet Buick GMC

  • Murray Chevrolet Winnipeg

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
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2025 CarGurus, Inc., All Rights Reserved.