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 Port Severn, ON

57 results
Midland, ON
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Bourgeois Midland Hyundai

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,516 kilometres

$51,500

Fair Deal
Midland, ON
2 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
29,516
Stock number:
00U505
VIN:
3GCUDCED2RG147514

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,211 kilometres

$43,995

Fair Deal
St. Catharines, ON
186 km 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 colour:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
75,211
Stock number:
18402
VIN:
3GCUDCED7PG362707

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,109 kilometres

$29,880

Good Deal
Woodbridge, ON
110 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
92,109
Stock number:
290265
VIN:
1GCRYCEF7KZ290265

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

128,850 kilometres

$34,995

Great Deal
Peterborough, ON
132 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
128,850
Stock number:
UT47774
VIN:
3GCPYCEK3NG147774

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,105 kilometres

$33,809

Great Deal
179 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
114,105
Stock number:
260274
VIN:
3GCPYCEK7NG216823

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,854 kilometres

$35,888

Good Deal
Mississauga, ON
128 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
118,854
Stock number:
um00412
VIN:
3GCPYCEK9NG100412

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,109 kilometres

$29,880

Good Deal
Woodbridge, ON
110 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
92,109
Stock number:
290265
VIN:
1GCRYCEF7KZ290265

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,510 kilometres

$44,498

Good Deal
Hamilton, ON
175 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Mileage:
84,510
Stock number:
CA240652
VIN:
3GCUDCED6RG130652

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

130,301 kilometres

$32,999

Good Deal
North Bay, ON
178 km away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Blue
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
130,301
Stock number:
26-252A
VIN:
1GCPYCEF0LZ121360

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,058 kilometres

$45,995

Good Deal
Belleville, ON
206 km 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 colour:
Black
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
44,058
Stock number:
43510J
VIN:
3GCPDCEKXRG200195

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,503 kilometres

$46,495

Good Deal
Belleville, ON
206 km 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 colour:
Black
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
36,503
Stock number:
43589J
VIN:
3GCPDCEK2RG107056

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab LB 4WD

73,187 kilometres

$44,722

Good Deal
Tillsonburg, ON
222 km 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 colour:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
73,187
Stock number:
T25221
VIN:
3GCUDCED1PG202645

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,742 kilometres

$43,990

Good Deal
Oakville, ON
141 km 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 colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
58,742
Stock number:
343583
VIN:
3GCUDCED8PG343583

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,205 kilometres

$41,995

Fair Deal
Cayuga, ON
201 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:
114,205
Stock number:
460150
VIN:
3GCPYCEL4NG120107

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,501 kilometres

$49,888

Fair Deal
Mississauga, ON
128 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:
Gray (Sterling Grey Metallic)
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
34,501
Stock number:
um40266
VIN:
3GCUDCED7RG140266

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,516 kilometres

$51,500

Fair Deal
Midland, ON
2 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
29,516
Stock number:
00U505
VIN:
3GCUDCED2RG147514

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,402 kilometres

$44,490

Fair Deal
Cobourg, ON
160 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:
Blue
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
21,402
Stock number:
NG661601
VIN:
3GCPDCEK6NG661601

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

109,440 kilometres

$39,900

Fair Deal
Bracebridge, ON
55 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
Combined gas mileage:
16 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
109,440
Stock number:
26151A
VIN:
1GCPYCEFXMZ274989

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

228,959 kilometres

$24,899

Fair Deal
Milton, ON
136 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Blue
Interior colour:
Black
Transmission:
Automatic
Mileage:
228,959
Stock number:
PR6257
VIN:
1GCPYCEFXKZ280420

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,884 kilometres

$41,995

Fair Deal
Guelph, ON
139 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
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
101,884
Stock number:
66742
VIN:
3GCPDCED1NG587361

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,510 kilometres

$44,498

Good Deal
Hamilton, ON
175 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Mileage:
84,510
Stock number:
CA240652
VIN:
3GCUDCED6RG130652

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Ontario
  6. / Port Severn
  • Chevrolet Silverado 1500 LT in Port Severn ON

  • Chevrolet Silverado 1500 RST in Port Severn ON

  • Chevrolet Silverado 1500 LT Trail Boss in Port Severn ON

  • Chevrolet Silverado 1500 Custom in Port Severn ON

  • Chevrolet Silverado 1500 High Country in Port Severn ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Port Severn ON

  • Chevrolet Silverado 1500 LTZ in Port Severn ON

  • Chevrolet Silverado 1500 Work Truck in Port Severn ON

  • Chevrolet Silverado 1500 LS in Port Severn ON

  • Chevrolet Silverado 1500 in Midland ON

  • Chevrolet Silverado 1500 in Barrie ON

  • Chevrolet Silverado 1500 in Innisfil ON

  • Chevrolet Silverado 1500 in Newmarket ON

  • Chevrolet Silverado 1500 in Owen Sound ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Orangeville ON

  • Chevrolet Silverado 1500 in Richmond Hill ON

  • Chevrolet Silverado 1500 in Vaughan ON

  • Chevrolet Silverado 1500 in Port Severn ON

  • Best Work Trucks for Sale in Port Severn ON

  • Chevrolet Trucks For Sale in Port Severn ON

  • Chevy Duramax Diesel Trucks for Sale in Port Severn ON

  • Chevrolet SUVs & Crossovers for Sale in Port Severn ON

  • Cheap Muscle Cars for Sale in Port Severn ON

  • 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 Port Severn ON

  • 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

  • Georgian Chevrolet Buick GMC

  • Orillia Chevrolet Buick GMC

  • Parry Sound Chevrolet Buick GMC

  • Tom Smith Chevrolet Buick GMC

  • Mike Jackson GM

  • Greavette Chevrolet Buick Cadillac GMC

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

© 2026 CarGurus, Inc., All Rights Reserved.