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 Custom Trail Boss for Sale near Madison, NY

142 results
Madison, NY
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Honesdale Chrysler

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,928 miles

$42,450

Fair Deal
Honesdale, PA
93 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Slate Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
13,928
Stock number:
PM109420
VIN:
3GCPKCEK2SG109420

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,505 miles

$33,999

Good Deal
Warrensburg, NY
96 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
44,505
Stock number:
6848PRA
VIN:
1GCPYCEF6MZ171584

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,000 miles

$24,995

Good Deal
Apalachin, NY
65 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
115,000
Stock number:
23924
VIN:
3GCPYCEF9LG201742

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,692 miles

$36,500

Good Deal
Williamson, NY
88 mi 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 color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
16,692
Stock number:
4285
VIN:
3GCPDCEK9NG691577

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,167 miles

$40,000

Good Deal
Williamson, NY
88 mi 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 color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
17,167
Stock number:
26207A
VIN:
3GCPDCEK2RG412735

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,283 miles

$33,500

Good Deal
Ballston Spa, NY
86 mi 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 color:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
50,283
Stock number:
T261083A
VIN:
3GCPDCEK9NG677923

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,505 miles

$33,999

Good Deal
Warrensburg, NY
96 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
44,505
Stock number:
6848PRA
VIN:
1GCPYCEF6MZ171584

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,381 miles

$34,000

Great Deal
Norwich, NY
26 mi 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 color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,381
Stock number:
0514UT
VIN:
3GCPDCEK7NG608843

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,273 miles

$36,937

Fair Deal
Liverpool, NY
43 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
37,273
Stock number:
S27988
VIN:
1GCPYCEF7MZ231047

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,068 miles

$32,995

Fair Deal
Herkimer, NY
28 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:
Blue
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
64,068
Stock number:
26202A
VIN:
1GCPYCEF6MZ379108

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,692 miles

$28,000

Great Deal
South Glens Falls, NY
98 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
70,692
Stock number:
WR6209
VIN:
1GCPYCEF0LZ358995

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,965 miles

$30,964

Fair Deal
Liverpool, NY
43 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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
63,965
Stock number:
S27981
VIN:
1GCPYCEFXKZ314193

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

117,787 miles

$23,000

Good Deal
Cortland, NY
41 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
117,787
Stock number:
S9572
VIN:
1GCRYCEF8KZ357732

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

60,888 miles

$29,779

Fair Deal
Hamilton, NY
4 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:
Cajun Red Tintcoat
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
60,888
Stock number:
P162A
VIN:
1GCRYCEF3LZ132877

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,300 miles

$31,994

Fair Deal
Bridgeport, NY
29 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:
Blue
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,300
Stock number:
B14172A
VIN:
1GCPYCEF2LZ148365

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,732 miles

$31,990

Fair Deal
Williamson, NY
88 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,732
Stock number:
26148C
VIN:
1GCPYCEF1MZ208928

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,300 miles

$31,994

Fair Deal
Bridgeport, NY
29 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:
Blue
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,300
Stock number:
B14172A
VIN:
1GCPYCEF2LZ148365

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / New York
  6. / Madison
  • Chevrolet Silverado 1500 LT in Madison NY

  • Chevrolet Silverado 1500 RST in Madison NY

  • Chevrolet Silverado 1500 LTZ in Madison NY

  • Chevrolet Silverado 1500 LT Trail Boss in Madison NY

  • Chevrolet Silverado 1500 LT1 in Madison NY

  • Chevrolet Silverado 1500 Custom in Madison NY

  • Chevrolet Silverado 1500 High Country in Madison NY

  • Chevrolet Silverado 1500 Custom Trail Boss in Madison NY

  • Chevrolet Silverado 1500 Work Truck in Madison NY

  • Chevrolet Silverado 1500 in Utica NY

  • Chevrolet Silverado 1500 in Syracuse NY

  • Chevrolet Silverado 1500 in Binghamton NY

  • Chevrolet Silverado 1500 in Ithaca NY

  • Chevrolet Silverado 1500 in Elmira NY

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Rochester NY

  • Chevrolet Silverado 1500 in Wilkes Barre PA

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Madison NY

  • Old Chevy Trucks for Sale in Madison NY

  • Classic Muscle Cars for Sale in Madison NY

  • Chevrolet Trucks For Sale in Madison NY

  • Cheap Muscle Cars for Sale in Madison NY

  • Work Trucks for Sale in Madison NY

  • Reliable Cars For Sale in Madison NY

  • American Made Trucks For Sale in Madison NY

  • Best Pickup Trucks For Sale in Madison NY

  • Best Cars Under $5,000 For Sale in Madison NY

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Madison NY

  • 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 in Madison

  • Used SUVs / Crossovers for Sale with Low Mileage in Madison

  • Used Hatchbacks for Sale with Low Mileage in Madison

  • Used Convertibles for Sale with Low Mileage in Madison

  • Used Vans for Sale with Low Mileage in Madison

  • Used Minivans for Sale with Low Mileage in Madison

  • Used Pickup Trucks for Sale with Low Mileage in Madison

  • Used Coupes for Sale with Low Mileage in Madison

  • Used Wagons for Sale with Low Mileage in Madison

  • NYE Automotive Group

  • Reymore Chevrolet Sales, Inc.

  • Maguire Chevrolet of Baldwinsville

  • Sharon Chevrolet, Inc.

  • Mastrovito Chevrolet

  • Sun 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.