Used Jeep Cherokee for Sale in Winchester, VA

Showing 24 of 40 listings

No matches found.

Save your search and we will notify you when we have cars that match your search criteria.

We expanded your search distance and we're unable to find cars that match.

Try adjusting your filters, or start a new search.

$21,400
$21,400 above
$631/mo est. ?
115,148 km

Tri-State Nissan

Authorized EpicVIN dealer

22602, Winchester VA

Check Details
$10,995
$10,995 above
$324/mo est. ?
212,840 km 3.2L

Global Pre-Owned Auto Sales

Authorized EpicVIN dealer

4.2 Google 50 reviews

25404, Martinsburg WV

Check Details
$10,995
$10,995 above
$324/mo est. ?
194,922 km 3.2L

Global Pre-Owned Auto Sales

Authorized EpicVIN dealer

4.2 Google 50 reviews

25404, Martinsburg WV

Check Details
$13,999
$13,999 above
$413/mo est. ?
214,251 km 3.2L

25427, Hedgesville WV

Check Details
$13,464
$13,464 above
$397/mo est. ?
110,026 km 2.4L

A2Z Auto Group

22602, Winchester VA

Check Details
$42,899
$42,899 above
$1,262/mo est. ?
0 km

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details
$26,998
$26,998 above
$796/mo est. ?
37,200 km

CarMax Winchester

22601, Winchester VA

Check Details
$40,399
$40,399 above
$1,189/mo est. ?
16 km

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details
Get a price quote
182,942 km

CMA's Toyota of Martinsburg

25401, Martinsburg WV

Check Details
$40,185
$40,185 above
$1,182/mo est. ?
24 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$37,495
$37,495 above
$1,103/mo est. ?
5 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$41,090
$41,090 above
$1,209/mo est. ?
0 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$36,310
$36,310 above
$1,068/mo est. ?
16 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$36,590
$36,590 above
$1,077/mo est. ?
16 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$8,495
$8,495 above
$251/mo est. ?
270,055 km

Auto Center Cars

22630, Front Royal VA

Check Details
$43,199
$43,199 above
$1,271/mo est. ?
0 km

22630, Front Royal VA

Check Details
$41,590
$41,590 above
$1,224/mo est. ?
11 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

Check Details
$17,699
$17,699 above
$522/mo est. ?
149,925 km

Honeycar

22602, Winchester VA

Check Details
$15,900
$15,900 above
$469/mo est. ?
159,373 km 2.4L

9 East Auto Sales LLC

25405, Martinsburg WV

Check Details
$43,799
$43,799 above
$1,289/mo est. ?
0 km

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details
$37,495
$37,495 above
$1,103/mo est. ?
16 km

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details
$37,596
$37,596 above
$1,106/mo est. ?
5 km

22603, Winchester VA

Check Details
Get a price quote
0 km 1.6L

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details
Get a price quote
0 km 1.6L

Criswell Chrysler Dodge Jeep Ram of Woodstock

4.0 Google 24 reviews

22664, Woodstock VA

Check Details

Frequently Asked Questions

Our marketplace currently lists 40 used cars in Winchester, VA from dealers and private sellers. Prices range from $8,340 to $37,530.

Top brands by active listings in Winchester, VA are Jeep. The mix often reflects local buying preferences.

The average listed price in Winchester, VA is $18,035. Browse by budget: under $10,000, under $20,000, or under $30,000.

No — you can buy from a seller in Winchester, VA regardless of your state of residence. You'll need to register and title the vehicle in your home state within the required window (usually 30 days). Local dealers typically handle paperwork for out-of-state buyers.

Yes — popular nearby options include cities across the state. You can also browse all used cars in Virginia.