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Used Jeep Cherokee for Sale near Windsor, VA

573 results
Windsor, VA
2014 Jeep Cherokee Trailhawk 4WD Heritage Motor Company - Shore Dr.

2014 Jeep Cherokee

Trailhawk 4WD

115,350 miles

$10,495

Fair Deal
Virginia Beach, VA
31 mi away
Year:
2014
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
115,350
Stock number:
18566
VIN:
1C4PJMBB3EW286268

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2016 Jeep Cherokee Sport 4WD

2016 Jeep Cherokee

Sport 4WD

156,890 miles

$7,995

Fair Deal
Petersburg, VA
43 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Blue
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
156,890
Stock number:
182636
VIN:
1C4PJMAB6GW182636

Sponsored

2017 Jeep Cherokee Trailhawk L Plus 4WD

2017 Jeep Cherokee

Trailhawk L Plus 4WD

135,161 miles

$9,495

Good Deal
Petersburg, VA
43 mi away
Year:
2017
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Red
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
135,161
Stock number:
515024
VIN:
1C4PJMBB9HW515024

Sponsored

2015 Jeep Cherokee Latitude 4WD

2015 Jeep Cherokee

Latitude 4WD

105,292 miles

$8,995

Good Deal
Petersburg, VA
43 mi away
Year:
2015
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
9-Speed Automatic
Mileage:
105,292
Stock number:
668157
VIN:
1C4PJMCS9FW668157

Preparing for a close up...

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2014 Jeep Cherokee

Trailhawk 4WD

115,350 miles

$10,495

Fair Deal
Virginia Beach, VA
31 mi away
Year:
2014
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
115,350
Stock number:
18566
VIN:
1C4PJMBB3EW286268

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Overland 4WD

114,667 miles

$7,995

Great Deal
Norfolk, VA
27 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
114,667
Stock number:
11615
VIN:
1C4PJMJS7GW339963

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2017 Jeep Cherokee

Limited FWD

94,362 miles

$11,300

Good Deal
Hopewell, VA
44 mi away
Year:
2017
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Transmission:
9-Speed Automatic
Mileage:
94,362
Stock number:
260165A
VIN:
1C4PJLDB3HW534238

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2021 Jeep Cherokee

Limited 4WD

34,104 miles

$21,599

Good Deal
Certified Pre-Owned
Prince George, VA
45 mi away
Year:
2021
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Bright White Clearcoat
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,104
Stock number:
A2097
VIN:
1C4PJMDX9MD219936

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Sport 4WD

156,890 miles

$7,995

Fair Deal
Petersburg, VA
43 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Blue
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
156,890
Stock number:
182636
VIN:
1C4PJMAB6GW182636

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Limited FWD

153,192 miles

$6,499

Good Deal
Norfolk, VA
27 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Brilliant Black Crystal Pearl Coat
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
9-Speed Automatic
Mileage:
153,192
VIN:
1C4PJLDBXGW319244

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2016 Jeep Cherokee

Latitude 4WD

131,431 miles

$8,995

Fair Deal
Norfolk, VA
29 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Black
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
9-Speed Automatic
Mileage:
131,431
Stock number:
16J2228
VIN:
1C4PJMCS9GW262798

Preparing for a close up...

Photos coming soon

2017 Jeep Cherokee

Trailhawk L Plus 4WD

135,161 miles

$9,495

Good Deal
Petersburg, VA
43 mi away
Year:
2017
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Red
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
135,161
Stock number:
515024
VIN:
1C4PJMBB9HW515024

Preparing for a close up...

Photos coming soon

2014 Jeep Cherokee

Limited 4WD

88,288 miles

$9,900

Good Deal
Virginia Beach, VA
31 mi away
Year:
2014
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Blue
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
88,288
VIN:
1C4PJMDSGEW276007

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Limited 4WD

184,979 miles

$7,161

Fair Deal
Chesapeake, VA
16 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Brilliant Black Crystal Pearlcoat
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
184,979
Stock number:
J260110606T1
VIN:
1C4PJMDB1GW267198

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  1. Home
  2. / Used Cars
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  4. / Virginia
  5. / Windsor
Overview
Reviews
FAQs

CarGurus recommends the 2019 Jeep Cherokee

Picture of Jeep Cherokee ## Summary - With 4,687 currently listed for sale on CarGurus and an **average price of $15,292.00**, 33.7% of 2019 Jeep Cherokees for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2019 Jeep Cherokee 4.47 / 5 stars. - **67.6% of 2019 Cherokee models on CarGurus are accident free**. - The 2019 Jeep Cherokee impresses with its blend of comfort and capability, featuring modular engine options, spacious interiors, and advanced technology that meets various needs for both city and off-road driving. ## Why it stands out The 2019 Jeep Cherokee stands out for its balanced blend of ruggedness and daily driveability, a hallmark of the Jeep brand known for its off-road prowess. This model year features a dynamic range of engine options, including a robust 2.0-liter turbocharged four-cylinder that provides impressive performance and fuel efficiency for any adventure. Owners often praise its roomy and comfortable interior, making it suitable for families or active lifestyles. Additionally, with a variety of trims available, from the well-equipped Latitude to the off-road-focused Trailhawk, buyers appreciate the flexibility the 2019 Jeep Cherokee offers to match diverse preferences and driving needs. Recognized for its reliability, this model continues to uphold the legacy of the Jeep brand combining utility and innovation seamlessly. ## Other model years to consider - **[2020 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2020-Jeep-Cherokee-c29396)** - Average price: $17,122.00 - Good/great deal percentage: 33.2% - User rating: 4.62 / 5 - Total listings: 5,148 - **[2018 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2018-Jeep-Cherokee-c27056)** - Average price: $13,516.00 - Good/great deal percentage: 32.7% - User rating: 4.39 / 5 - Total listings: 4,266 - **[2022 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2022-Jeep-Cherokee-c32108)** - Average price: $23,479.00 - Good/great deal percentage: 31.1% - User rating: 4.82 / 5 - Total listings: 2,608 These recommendations are based on CarGurus' proprietary market data from February 9, 2026, CarGurus experts' opinions, and generative AI.

4.4 Overall rating

(1,108 reviews)

Customers say

The Jeep Cherokee has long been celebrated for its rugged reliability, impressive off-road capabilities, and overall durability. Owners tend to praise its powerful engines, spacious interiors, and user-friendly features across various models. Many drivers also appreciate the comfortable ride and the great value it offers. However, some common complaints include inconsistent performance, fuel economy concerns, and occasional reliability issues, particularly with older models. In essence, the Cherokee stands out as a dependable choice for those who enjoy adventure and need a versatile vehicle, though it may not always deliver on efficiency and peak performance.

AI generated from the text of customer reviews.

What people say

interior off-road capabilities performance power reliability
Stephanie F
5.0
Reviewed a 2016 Jeep Cherokee on Jun 05, 2024

My husband and I absolutely enjoy this new car of ours. This is the vehicle we want and need. The features are perfect and everything works great, though we had to replace the brakes, spark plugs , and a few other things. The vehicle is in excellent condition and still looks new. The interior is beautiful. It’s the best vehicle for all of the driving that we do.

Xing F
5.0
Reviewed a 2021 Jeep Cherokee on Oct 22, 2024

The 2021 Jeep Cherokee is a versatile compact SUV that excels in off-road performance, particularly in the Trailhawk trim, thanks to its advanced 4x4 system and terrain management features.

Jeremy R
5.0
Reviewed a 2022 Jeep Cherokee on Aug 14, 2024

The cars features are great it rides nice and had a one stop shop for everything we wanted in a family vehicle couldnt be happier

Michael W
5.0
Reviewed a 2020 Jeep Trailhawk Elite 4WD on Jul 28, 2024

The vehicle is very capable on and off road. Plenty of power to get up to speed on the highway, pass someone, and 4500lb towing capacity. Also it is the only trailhawk in the lineup to have a true rear locker.

Matthew P
5.0
Reviewed a 2021 Jeep Cherokee on Dec 29, 2024

The car’s features are awesome, all this at a great deal

Jeep Cherokee FAQs

How much does the Jeep Cherokee cost in Windsor, VA?

The average Jeep Cherokee costs about $15,549.02. The average price has decreased by -9.3% since last year. The 573 for sale near Windsor, VA on CarGurus, range from $3,511 to $100,288 in price.

How many Jeep Cherokee vehicles in Windsor, VA have no reported accidents or damage?

519 out of 573 for sale near Windsor, VA have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

  • 2026 Jeep Cherokee in Windsor VA

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