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  *Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
  
  
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  Used
  Chevrolet Silverado 1500 Custom Trail Boss
  for sale
  
  
    near
Woodbury, CT 
    
  
      - Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
    
  *Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
  
  
  **Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
  
Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Was contacted by Zach from Waterbury dealership.
Was contacted by Zach from Waterbury dealership. Right off the bat I felt like he understood my needs and wanted to work a fair deal for the sale of my truck. We got it done and myself into new Colorado. Staff was very helpful and patient. I would recommend this dealership team to anyone. Thanks!!
Thumbs up
Since I've owned it, so far so good. I like my truck and I appreciate it everyday. A little bit of shaking in the steering at high speeds but I'm not concerned with it. Overall, pretty great.
Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
The sales staff and the management with above and beyond
The sales staff and the management with above and beyond their duties to make sure that my new vehicle purchase went very smooth. Will definitely come back.
I have a 2020 1500 RST with the 5.
I have a 2020 1500 RST with the 5.3 engine and 8 speed transmission. My truck now has 67,000 miles. The acceleration is outstanding and smooth from gears 3-8. Probably could use more torque for gears 1-2, but not weak by any means. I have had no mechanical problems outside of the clunking rear suspension which was fixed by retorqueing the rear leaf spring suspension bolts. Other than that minor issue, it has been very reliable. I have heard these transmissions have had issues, but nothing that has caused issues for me. It has the 60-70 MPH shutter that is common to these transmissions, but I have learned how to drive to avoid the shutter, as I did with my 2011 1500. Overall pretty satisfied at this point. Comfort and amenities could be better for the front seats for the price, but I bought it knowing that. FYI my front brakes at this point are still 50%, and I have invested very little outside of a few fluid exchanges and routine maintenance. Excellent fuel mileage: 20 mpg with 50% highway vs city driving.
 
          
        
       
          
        
       
          
        
       
          
        
       
          
        
       
            Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Justin at Ingersoll was wonderful to deal with, he is
Justin at Ingersoll was wonderful to deal with, he is knowledgable and caring. Dom the manager came out to introduce himself and welcome us. Ellie went out of her way for us re our new registration.
My 2024 Chevy Silverado LTZ provides a deluxe large SUV
My 2024 Chevy Silverado LTZ provides a deluxe large SUV interior and a standard (short) tuck bed all in one vehicle. It is loaded with features to make it look and operate very well, and it provides mid 20's regular unleaded fuel mileage. The dynamic fuel management system combined with the 10 speed automatic transmission work together flawlessly to deliver smooth power without being able to realize what gear or how many cylinders the powertrain is using at any given time.
There are additional matching cars outside your search area.
Partial matches are generated by applying your search criteria to a larger search area. Our goal is to help you discover additional cars that match your search preferences.
As a benefit to some of our dealer customers, we display their listings first.
 
          
        
       
          
        
       
          
        
       
          
        
       
          
        
       
            Used
2021 Chevrolet Silverado 1500 Custom Trail Boss
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2021 Chevrolet Silverado 1500 Custom Trail Boss
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2024 Chevrolet Silverado 1500 Custom Trail Boss
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2021 Chevrolet Silverado 1500 Custom Trail Boss
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            Chevrolet Certified
2023 Chevrolet Silverado 1500 Custom Trail Boss
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            Certified
2021 Chevrolet Silverado 1500 Custom Trail Boss
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            Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
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            Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
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            Chevrolet Certified
2021 Chevrolet Silverado 1500 Custom Trail Boss
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2024 Chevrolet Silverado 1500 Custom Trail Boss
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  *Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
  
  
  **Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
  
Chevrolet Silverado 1500 Custom Trail Boss by city
- 
  
    Chevrolet Silverado 1500 Custom Trail Boss in Woodbury, CT
  
  1 Great Deal out of 23 listings starting at $26,963 
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  1 Great Deal out of 23 listings starting at $26,963 
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  1 Great Deal out of 23 listings starting at $26,963 
Chevrolet Silverado 1500 by trim
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    Chevrolet Silverado 1500 LT
  
  14 Great Deals out of 78 listings starting at $8,491 
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    Chevrolet Silverado 1500 RST
  
  1 Great Deal out of 38 listings starting at $25,539 
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    Chevrolet Silverado 1500 LTZ
  
  1 Great Deal out of 20 listings starting at $19,811 
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This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.
