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 Saybrook, IL

172 results
Saybrook, IL
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Chevrolet of Merrillville

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,460 miles

$28,990

Fair Deal
Merrillville, IN
97 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,460
Stock number:
8887A
VIN:
1GCPYCEH8MZ430612

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$32,497

Great Deal
Orland Park, IL
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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,704
Stock number:
B10901
VIN:
1GCPYCEF7MZ410785

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

105,286 miles

$27,600

Good Deal
Oak Forest, IL
90 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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
105,286
Stock number:
45388AA
VIN:
3GCPYCEF2MG312960

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,741 miles

$35,540

Fair Deal
Lafayette, IN
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:
Red
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
41,741
Stock number:
Q499
VIN:
1GCPYCEFXMZ252555

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,909 miles

$30,980

Good Deal
Peoria, IL
63 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
41,909
Stock number:
K115023A
VIN:
1GCPYCEH9LZ149983

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,173 miles

$28,460

Good Deal
Morton, IL
51 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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,173
Stock number:
G26310B
VIN:
1GCPYCEF1MZ169290

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,243 miles

$39,900

Fair Deal
Bradley, IL
62 mi 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 color:
Red Hot G7c
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
8-Speed Automatic
Mileage:
15,243
Stock number:
p3665
VIN:
3GCPDCEKXPG195562

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,931 miles

$30,400

Good Deal
Morton, IL
51 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
66,931
Stock number:
G26242B
VIN:
3GCPYCEK9NG126296

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,041 miles

$45,588

Fair Deal
Certified Pre-Owned
Morris, IL
61 mi 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 color:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
8,041
Stock number:
C4927A
VIN:
3GCUKCED5SG297418

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,552 miles

$34,990

Good Deal
Bloomington, IL
23 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
22,552
Stock number:
QBP4609A
VIN:
3GCPDCEK8NG686354

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

87,409 miles

$30,988

Good Deal
Mendota, IL
83 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Silver Ice Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
87,409
Stock number:
C539101
VIN:
1GCPYCELXMZ344111

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$32,497

Great Deal
Orland Park, IL
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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,704
Stock number:
B10901
VIN:
1GCPYCEF7MZ410785

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,478 miles

$45,299

Fair Deal
Certified Pre-Owned
Sandwich, IL
84 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Red Hot
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
13,478
Stock number:
P7424
VIN:
3GCUDCE88RG424900

Sponsored

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

  • Chevrolet Silverado 1500 LT in Saybrook IL

  • Chevrolet Silverado 1500 RST in Saybrook IL

  • Chevrolet Silverado 1500 LTZ in Saybrook IL

  • Chevrolet Silverado 1500 LT Trail Boss in Saybrook IL

  • Chevrolet Silverado 1500 LT1 in Saybrook IL

  • Chevrolet Silverado 1500 Custom in Saybrook IL

  • Chevrolet Silverado 1500 High Country in Saybrook IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Saybrook IL

  • Chevrolet Silverado 1500 Work Truck in Saybrook IL

  • Chevrolet Silverado 1500 in Bloomington IL

  • Chevrolet Silverado 1500 in Champaign IL

  • Chevrolet Silverado 1500 in Decatur IL

  • Chevrolet Silverado 1500 in Peoria IL

  • Chevrolet Silverado 1500 in Springfield IL

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Terre Haute IN

  • Chevrolet Silverado 1500 in Crawfordsville IN

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Saybrook IL

  • Old Chevy Trucks for Sale in Saybrook IL

  • Classic Muscle Cars for Sale in Saybrook IL

  • Chevrolet Trucks For Sale in Saybrook IL

  • Cheap Muscle Cars for Sale in Saybrook IL

  • Work Trucks for Sale in Saybrook IL

  • Reliable Cars For Sale in Saybrook IL

  • American Made Trucks For Sale in Saybrook IL

  • Best Pickup Trucks For Sale in Saybrook IL

  • Best Cars Under $5,000 For Sale in Saybrook IL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Saybrook IL

  • 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

  • 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

  • Sam Leman Chevrolet Champaign

  • Sam Leman Chevrolet

  • Barker Chevrolet Inc

  • Petersen Chevrolet Buick

  • Country Chevrolet

  • Ridings Chevy Buick CDJR

  • Baum Chevrolet Buick

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.