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 Woodstock, ON

37 results
Woodstock, ON
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Queenston Chevrolet Buick GMC

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,726 kilometres

$46,998

Fair Deal
Hamilton, ON
78 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Mileage:
81,726
Stock number:
CA240652
VIN:
3GCUDCED6RG130652

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

228,959 kilometres

$24,499

Fair Deal
Milton, ON
83 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

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

138,522 kilometres

$36,995

Fair Deal
Cayuga, ON
72 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
Transmission:
Automatic
Mileage:
138,522
Stock number:
451627
VIN:
1GCPYCEF3MZ254664

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,613 kilometres

$39,198

Good Deal
Grimsby, ON
100 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:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
72,613
Stock number:
P226855
VIN:
3GCPYCEK2NG116855

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,593 kilometres

$42,995

Good Deal
Listowel, ON
70 km 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 colour:
White
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
35,593
Stock number:
P7155
VIN:
3GCPDCEK3PG297155

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,839 kilometres

$44,777

Good Deal
32 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
68,839
Stock number:
251484
VIN:
3GCUDCED8RG386064

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,995 kilometres

$36,433

Good Deal
London, ON
38 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
Transmission:
8-Speed Automatic
Mileage:
99,995
Stock number:
15-U1184
VIN:
3GCPYCEK6NG112775

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,854 kilometres

$35,888

Good Deal
Mississauga, ON
96 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,093 kilometres

$56,284

Good Deal
Certified Pre-Owned
Exeter, ON
64 km away
Year:
2025
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
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
16,093
Stock number:
101820
VIN:
3GCUKCED0SG133879

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,475 kilometres

$37,995

Good Deal
Guelph, ON
57 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
95,475
Stock number:
A05011
VIN:
1GCPYCEF8MZ421536

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,538 kilometres

$38,995

Good Deal
Stratford, ON
31 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Mileage:
79,538
Stock number:
TC3530A
VIN:
3GCPYCEK5NG131849

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,110 kilometres

$39,786

Good Deal
Oakville, ON
97 km 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 colour:
Black
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
63,110
Stock number:
307318
VIN:
3GCPDCEK2PG307318

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,750 kilometres

$41,950

Fair Deal
Guelph, ON
56 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:
65,750
Stock number:
NG627763
VIN:
3GCPDCEK5NG627763

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,000 kilometres

$50,998

Fair Deal
Guelph, ON
56 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
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
23,000
Stock number:
RG440171
VIN:
3GCUDCED6RG440171

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,050 kilometres

$38,988

Fair Deal
Guelph, ON
56 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:
95,050
Stock number:
NG521623
VIN:
3GCPDCEK7NG521623

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

138,522 kilometres

$36,995

Fair Deal
Cayuga, ON
72 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
Transmission:
Automatic
Mileage:
138,522
Stock number:
451627
VIN:
1GCPYCEF3MZ254664

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,000 kilometres

$50,998

Fair Deal
Guelph, ON
56 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
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
23,000
Stock number:
RG440171
VIN:
3GCUDCED6RG440171

Sponsored

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

  • Chevrolet Silverado 1500 LT in Woodstock ON

  • Chevrolet Silverado 1500 RST in Woodstock ON

  • Chevrolet Silverado 1500 LT Trail Boss in Woodstock ON

  • Chevrolet Silverado 1500 Custom in Woodstock ON

  • Chevrolet Silverado 1500 High Country in Woodstock ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Woodstock ON

  • Chevrolet Silverado 1500 LTZ in Woodstock ON

  • Chevrolet Silverado 1500 Work Truck in Woodstock ON

  • Chevrolet Silverado 1500 LS in Woodstock ON

  • Chevrolet Silverado 1500 in Brantford ON

  • Chevrolet Silverado 1500 in Kitchener ON

  • Chevrolet Silverado 1500 in London ON

  • Chevrolet Silverado 1500 in Cambridge ON

  • Chevrolet Silverado 1500 in Guelph ON

  • Chevrolet Silverado 1500 in Listowel ON

  • Chevrolet Silverado 1500 in Hamilton ON

  • Chevrolet Silverado 1500 in Selkirk ON

  • Chevrolet Silverado 1500 in Cayuga ON

  • Chevrolet Silverado 1500 in Woodstock ON

  • Best Work Trucks for Sale in Woodstock ON

  • Chevrolet Trucks For Sale in Woodstock ON

  • Chevy Duramax Diesel Trucks for Sale in Woodstock ON

  • Chevrolet SUVs & Crossovers for Sale in Woodstock ON

  • Cheap Muscle Cars for Sale in Woodstock 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 Woodstock 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

  • Strickland's

  • Barry Cullen Chevrolet Cadillac Ltd

  • Leggat Chevrolet Cadillac Buick GMC

  • Queenston Chevrolet Buick GMC

  • Scherer Chevrolet Buick GMC

  • Robinson Chevrolet Buick GMC Simcoe

  • Robinson Auto Group

  • Searles Chevrolet

  • DeGroote-Hill Chevrolet Buick GMC Ltd.

  • Disbrowe Chevrolet Buick GMC Cadillac

  • Robinson Chevrolet

  • Huron Motor Products Ltd

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.