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 High Country for Sale near Upton, MA

224 results
Upton, MA
2022 Chevrolet Silverado 1500 High Country Crew Cab 4WD CarNova Of Southborough

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

52,110 miles

$42,268

Good Deal
Southborough, MA
9 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
52,110
Stock number:
604931
VIN:
1GCUDJEL6NZ604931

Sponsored

2017 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2017 Chevrolet Silverado 1500

High Country Crew Cab 4WD

98,539 miles

$26,995

Fair Deal
Brockton, MA
29 mi away
Year:
2017
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 (Graphite Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black Medium Ash Gray Piping Stitching
Transmission:
8-Speed Automatic Overdrive
Mileage:
98,539
Stock number:
HY3508
VIN:
3GCUKTEC9HG394007

Sponsored

2024 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2024 Chevrolet Silverado 1500

High Country Crew Cab 4WD

30,305 miles

$50,647

Good Deal
Mendon, MA
5 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
30,305
Stock number:
47923
VIN:
1GCUDJEL8RZ239688

Sponsored

2020 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2020 Chevrolet Silverado 1500

High Country Crew Cab 4WD

78,373 miles

$33,924

Good Deal
Raynham, MA
36 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
78,373
Stock number:
B7780A
VIN:
1GCUYHED2LZ274594

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

15,019 miles

$46,561

Good Deal
Putnam, CT
22 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
15,019
Stock number:
26487A
VIN:
3GCUYHEL9NG172008

Preparing for a close up...

Photos coming soon

2016 Chevrolet Silverado 1500

High Country Crew Cab 4WD

72,276 miles

$26,980

Great Deal
Whitman, MA
33 mi away
Year:
2016
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
72,276
Stock number:
83821hp
VIN:
3GCUKTEJ6GG383821

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

High Country Crew Cab 4WD

99,668 miles

$29,862

Great Deal
Wellesley, MA
17 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Havana Brown Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
99,668
Stock number:
P0122
VIN:
1GCUYHEL7KZ108965

Preparing for a close up...

Photos coming soon

2017 Chevrolet Silverado 1500

High Country Crew Cab 4WD

124,922 miles

$22,995

Great Deal
Cranston, RI
27 mi away
Year:
2017
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
124,922
Stock number:
13507
VIN:
3GCUKTEJ4HG514875

Preparing for a close up...

Photos coming soon

2017 Chevrolet Silverado 1500

High Country Crew Cab 4WD

105,675 miles

$26,999

Good Deal
Taunton, MA
32 mi away
Year:
2017
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Blue
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
105,675
Stock number:
01-414593
VIN:
3GCUKTEJ9HG414593

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

High Country Crew Cab 4WD

85,293 miles

$33,877

Good Deal
Palmer, MA
37 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
85,293
Stock number:
V15933B
VIN:
1GCUYHEL1LZ209064

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

High Country Crew Cab 4WD

75,139 miles

$34,495

Fair Deal
Milford, MA
4 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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
75,139
Stock number:
189799
VIN:
3GCUYHED0KG227711

Preparing for a close up...

Photos coming soon

2017 Chevrolet Silverado 1500

High Country Crew Cab 4WD

98,539 miles

$26,995

Fair Deal
Brockton, MA
29 mi away
Year:
2017
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 (Graphite Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black Medium Ash Gray Piping Stitching
Transmission:
8-Speed Automatic Overdrive
Mileage:
98,539
Stock number:
HY3508
VIN:
3GCUKTEC9HG394007

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

81,343 miles

$34,995

Good Deal
Framingham, MA
13 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:
Jet Black
Transmission:
Automatic
Mileage:
81,343
Stock number:
CTR211988A
VIN:
1GCUYHEL6NZ205174

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

19,469 miles

$50,774

Good Deal
Chicopee, MA
50 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
19,469
Stock number:
G263042A
VIN:
1GCUDJE89PZ185682

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

High Country Crew Cab 4WD

96,172 miles

$32,543

Good Deal
Lynn, MA
38 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
96,172
Stock number:
AT42175A
VIN:
3GCUYHELXLG234321

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

High Country Crew Cab 4WD

99,668 miles

$29,862

Great Deal
Wellesley, MA
17 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Havana Brown Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
99,668
Stock number:
P0122
VIN:
1GCUYHEL7KZ108965

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / High Country
  5. / Massachusetts
  6. / Upton
  • Chevrolet Silverado 1500 LT in Upton MA

  • Chevrolet Silverado 1500 RST in Upton MA

  • Chevrolet Silverado 1500 LTZ in Upton MA

  • Chevrolet Silverado 1500 LT Trail Boss in Upton MA

  • Chevrolet Silverado 1500 LT1 in Upton MA

  • Chevrolet Silverado 1500 High Country in Upton MA

  • Chevrolet Silverado 1500 Custom in Upton MA

  • Chevrolet Silverado 1500 Custom Trail Boss in Upton MA

  • Chevrolet Silverado 1500 Work Truck in Upton MA

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Boston MA

  • Chevrolet Silverado 1500 in New Bedford MA

  • Chevrolet Silverado 1500 in Plymouth MA

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Manchester NH

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Upton MA

  • Old Chevy Trucks for Sale in Upton MA

  • Classic Muscle Cars for Sale in Upton MA

  • Chevrolet Trucks For Sale in Upton MA

  • Cheap Muscle Cars for Sale in Upton MA

  • Work Trucks for Sale in Upton MA

  • Reliable Cars For Sale in Upton MA

  • American Made Trucks For Sale in Upton MA

  • Best Pickup Trucks For Sale in Upton MA

  • Best Cars Under $5,000 For Sale in Upton MA

  • 2019 Chevrolet Silverado 1500 High Country in Upton MA

  • 2018 Chevrolet Silverado 1500 High Country in Upton MA

  • 2017 Chevrolet Silverado 1500 High Country in Upton MA

  • 2016 Chevrolet Silverado 1500 High Country in Upton MA

  • 2015 Chevrolet Silverado 1500 High Country in Upton MA

  • 2014 Chevrolet Silverado 1500 High Country in Upton MA

  • 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

  • Herb Connolly Chevrolet

  • Hurd Auto Mall

  • Diamond Auto Group

  • Herb Chambers Chevrolet of Danvers

  • Bill Deluca Chevrolet Cadillac

  • Copeland Chevrolet

  • Colonial West Chevrolet

  • Nucar Chevrolet of Woburn

  • Commonwealth Motors

  • Pride Chevrolet

  • Colonial Chevrolet

  • Copeland Chevrolet Hudson

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.