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 Middlefield, CT

223 results
Middlefield, CT
2021 Chevrolet Silverado 1500 High Country Crew Cab 4WD Blasius Mitsubishi

2021 Chevrolet Silverado 1500

High Country Crew Cab 4WD

25,589 miles

$41,487

Great Deal
Brookfield, CT
36 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
25,589
Stock number:
Z4078
VIN:
1GCUYHEL3MZ301584

Sponsored

2022 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

68,514 miles

$39,894

Good Deal
Waterbury, CT
18 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:
Cherry Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
68,514
Stock number:
U9813
VIN:
1GCUDJEL3NZ557468

Sponsored

2022 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

22,606 miles

$45,899

Good Deal
Waterbury, CT
18 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:
Dark Ash Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
22,606
Stock number:
U10114
VIN:
1GCUDJEL6NZ595745

Sponsored

2022 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

57,694 miles

$37,900

Good Deal
Branford, CT
15 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
White (Iridescent Pearl Tricoat)
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
57,694
Stock number:
11574
VIN:
3GCUYHEL2NG108327

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

56,783 miles

$40,562

Good Deal
Norwich, CT
32 mi 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 color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
56,783
Stock number:
7055
VIN:
3GCUYHED7NG164546

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

18,680 miles

$47,608

Good Deal
Brookfield, CT
36 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
18,680
Stock number:
Z4177
VIN:
1GCUDJEL1PZ182859

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

High Country Crew Cab 4WD

87,616 miles

$32,980

Great Deal
East Hartford, CT
18 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
87,616
Stock number:
U00484
VIN:
3GCUYHED9MG457749

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

High Country Crew Cab 4WD

125,747 miles

$24,924

Great Deal
Naugatuck, CT
16 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
125,747
Stock number:
262851T
VIN:
3GCUYHEL5KG262851

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

49,951 miles

$41,443

Good Deal
Brookfield, CT
36 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
49,951
Stock number:
Z4211
VIN:
3GCUDJEL2NG518807

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

High Country Crew Cab 4WD

120,930 miles

$29,980

Good Deal
East Hartford, CT
18 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
120,930
Stock number:
U00502
VIN:
1GCUYHEL3MZ148723

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

55,509 miles

$42,549

Great Deal
Waterbury, CT
18 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
55,509
Stock number:
U9909
VIN:
1GCUDJE82PZ117630

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

33,701 miles

$46,978

Good Deal
Watertown, CT
20 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Northsky Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
33,701
Stock number:
K3148
VIN:
1GCUDJED9PZ130243

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

High Country Crew Cab 4WD

27,610 miles

$51,900

Fair Deal
Branford, CT
15 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
27,610
Stock number:
326831SA
VIN:
1GCUDJEL5RZ326545

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

29,714 miles

$47,758

Good Deal
Pawling, NY
45 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,714
Stock number:
A290672
VIN:
1GCUDJELXPZ290672

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

High Country Crew Cab 4WD

55,570 miles

$37,788

Good Deal
Waterbury, CT
15 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
55,570
Stock number:
51879AQ
VIN:
3GCUYHELXMG476849

Preparing for a close up...

Photos coming soon

2017 Chevrolet Silverado 1500

High Country Crew Cab 4WD

138,411 miles

$21,995

Good Deal
Waterbury, CT
19 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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
138,411
VIN:
3GCUKTEC5HG204610

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

68,514 miles

$39,894

Good Deal
Waterbury, CT
18 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:
Cherry Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
68,514
Stock number:
U9813
VIN:
1GCUDJEL3NZ557468

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

High Country Crew Cab 4WD

27,610 miles

$51,900

Fair Deal
Branford, CT
15 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Nightshift Blue
Transmission:
Automatic
Mileage:
27,610
Stock number:
326831SA
VIN:
1GCUDJEL5RZ326545

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / High Country
  5. / Connecticut
  6. / Middlefield

  • Chevrolet Silverado 1500 LT in Middlefield CT

  • Chevrolet Silverado 1500 RST in Middlefield CT

  • Chevrolet Silverado 1500 LTZ in Middlefield CT

  • Chevrolet Silverado 1500 LT Trail Boss in Middlefield CT

  • Chevrolet Silverado 1500 LT1 in Middlefield CT

  • Chevrolet Silverado 1500 High Country in Middlefield CT

  • Chevrolet Silverado 1500 Custom in Middlefield CT

  • Chevrolet Silverado 1500 Custom Trail Boss in Middlefield CT

  • Chevrolet Silverado 1500 Work Truck in Middlefield CT

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Holtsville NY

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Middlefield CT

  • Old Chevy Trucks for Sale in Middlefield CT

  • Classic Muscle Cars for Sale in Middlefield CT

  • Chevrolet Trucks For Sale in Middlefield CT

  • Cheap Muscle Cars for Sale in Middlefield CT

  • Work Trucks for Sale in Middlefield CT

  • Reliable Cars For Sale in Middlefield CT

  • American Made Trucks For Sale in Middlefield CT

  • Best Pickup Trucks For Sale in Middlefield CT

  • Best Cars Under $5,000 For Sale in Middlefield CT

  • 2019 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 2018 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 2017 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 2016 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 2015 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 2014 Chevrolet Silverado 1500 High Country in Middlefield CT

  • 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

  • Richard Chevrolet

  • Ingersoll Auto of Pawling

  • Balise Chevrolet GMC

  • Central Chevrolet Inc

  • Grossman Chevrolet

  • Sullivan's Northwest Hills Chevy Cadillac Buick GMC

  • Key Chevrolet

  • Karl Chevrolet

  • Maritime Chevrolet

  • O'Neills Chevrolet

  • Eagle Chevrolet of Riverhead

  • East Hartford 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.