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 Oro-Medonte, ON

56 results
Tiny, ON
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Mark Wilson's Better Used Cars

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,050 kilometres

$38,988

Fair Deal
Guelph, ON
112 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

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,896 kilometres

$33,888

Good Deal
158 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:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
129,896
Stock number:
251613
VIN:
3GCPDCEK4NG545040

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

127,927 kilometres

$36,995

Good Deal
Richmond Hill, ON
66 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
6-Speed Automatic
Mileage:
127,927
Stock number:
U120881
VIN:
3GCPYCEFXMG120881

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,538 kilometres

$38,995

Great Deal
Stratford, ON
154 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

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

Great Deal
Woodbridge, ON
75 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,248 kilometres

$41,500

Good Deal
St Catharines, ON
150 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
Transmission:
Automatic
Mileage:
77,248
Stock number:
E2129
VIN:
3GCPDCED5NG520097

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

127,927 kilometres

$36,995

Good Deal
Richmond Hill, ON
66 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
6-Speed Automatic
Mileage:
127,927
Stock number:
U120881
VIN:
3GCPYCEFXMG120881

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,572 kilometres

$37,999

Good Deal
Mississauga, ON
102 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Northsky Blue (MET)
Interior colour:
Cloth - Jet Black
Transmission:
Automatic
Mileage:
114,572
Stock number:
226082TU
VIN:
1GCPYCEF6MZ226082

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,172 kilometres

$51,995

Good Deal
Certified Pre-Owned
Orillia, ON
29 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior colour:
Gray
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Transmission:
Automatic
Mileage:
39,172
Stock number:
TG152646A
VIN:
3GCUDCE81RG426116

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,767 kilometres

$48,998

Good Deal
Thornhill, ON
76 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
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
26,767
Stock number:
TA182319
VIN:
3GCPDCEK9RG182319

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,896 kilometres

$33,888

Good Deal
158 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:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
129,896
Stock number:
251613
VIN:
3GCPDCEK4NG545040

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,561 kilometres

$46,994

Good Deal
Bolton, ON
65 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:
Gray
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
38,561
Stock number:
U7411
VIN:
3GCPDCEK1RG237040

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,593 kilometres

$42,498

Good Deal
Listowel, ON
123 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,093 kilometres

$56,284

Good Deal
Certified Pre-Owned
Exeter, ON
186 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

140,814 kilometres

$34,900

Good Deal
Peterborough, ON
115 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:
140,814
Stock number:
118294
VIN:
3GCPYCEF7MG118294

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,594 kilometres

$46,490

Good Deal
Cobourg, ON
134 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
70,594
Stock number:
RG130718
VIN:
3GCUDCEDXRG130718

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
106 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

80,130 kilometres

$37,700

Good Deal
Mississauga, ON
83 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:
80,130
Stock number:
250006
VIN:
3GCPYCEK5NG183885

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
94 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,839 kilometres

$44,777

Good Deal
158 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,952 kilometres

$49,995

Fair Deal
Certified Pre-Owned
Brampton, ON
78 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:
White
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
30,952
Stock number:
124795A
VIN:
3GCPDCEK9RG373500

Sponsored

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

  • Chevrolet Silverado 1500 RST in Oro-Medonte ON

  • Chevrolet Silverado 1500 LT Trail Boss in Oro-Medonte ON

  • Chevrolet Silverado 1500 Custom in Oro-Medonte ON

  • Chevrolet Silverado 1500 High Country in Oro-Medonte ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Oro-Medonte ON

  • Chevrolet Silverado 1500 LTZ in Oro-Medonte ON

  • Chevrolet Silverado 1500 Work Truck in Oro-Medonte ON

  • Chevrolet Silverado 1500 LS in Oro-Medonte ON

  • Chevrolet Silverado 1500 in Barrie ON

  • Chevrolet Silverado 1500 in Innisfil ON

  • Chevrolet Silverado 1500 in Midland ON

  • Chevrolet Silverado 1500 in Newmarket ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Richmond Hill ON

  • Chevrolet Silverado 1500 in Vaughan ON

  • Chevrolet Silverado 1500 in Unionville ON

  • Chevrolet Silverado 1500 in Orangeville ON

  • Chevrolet Silverado 1500 in Oro-Medonte ON

  • Best Work Trucks for Sale in Oro-Medonte ON

  • Chevrolet Trucks For Sale in Oro-Medonte ON

  • Chevy Duramax Diesel Trucks for Sale in Oro-Medonte ON

  • Chevrolet SUVs & Crossovers for Sale in Oro-Medonte ON

  • Cheap Muscle Cars for Sale in Oro-Medonte 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 Oro-Medonte 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

  • Roy Foss Motors Ltd.

  • Wilson-Niblett

  • Royal Chevrolet Cadillac

  • NewRoads Chevrolet Cadillac Buick GMC

  • Orillia Chevrolet Buick GMC

  • Highland Chevrolet Buick GMC Cadillac

  • Williamson GM Uxbridge

  • Tom Smith Chevrolet Buick GMC

  • Eastside Chevrolet Buick GMC Ltd

  • Bolton GM

  • Mike Jackson GM

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.