Used Jeep Grand Cherokee L for Sale in Oakland, MD

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$37,995
$37,995 above
$1,120/mo est. ?
41,284 km 3.6L

Timbrook Ford of Oakland

Authorized EpicVIN dealer

4.3 Google 59 reviews

21550, Oakland MD

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$30,993
$30,993 above
$914/mo est. ?
30,025 km 3.6L

Timbrook Ford

Authorized EpicVIN dealer

4.7 Google 205 reviews

26726, Keyser WV

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$45,337
$45,337 above
$1,334/mo est. ?
8 km 3.6L

Auto Land Chrysler Dodge Jeep Ram

3.9
Star icon
3 reviews
4.5 Google 34 reviews

21520, Accident MD

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$49,990
$49,990 above
$1,471/mo est. ?
35 km

Patriot Chrysler Jeep

4.7 Google 197 reviews

21550, Oakland MD

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$49,630
$49,630 above
$1,460/mo est. ?
0 km

Weimer Chrysler Dodge Jeep Ram of Keyser

26726, Keyser WV

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$56,690
$56,690 above
$1,668/mo est. ?
43 km

Patriot Automotive Group

21550, Oakland MD

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$53,839
$53,839 above
$1,584/mo est. ?
27 km

Patriot Automotive Group

21550, Oakland MD

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$45,872
$45,872 above
$1,350/mo est. ?
0 km

Patriot Chrysler Jeep

4.7 Google 197 reviews

21550, Oakland MD

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$36,760
$36,760 above
$1,084/mo est. ?
30,516 km

Patriot Automotive Group

21550, Oakland MD

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$52,445
$52,445 above
$1,543/mo est. ?
0 km

Auto Max Chrysler Dodge Jeep RAM

26537, Kingwood WV

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$31,169
$31,169 above
$919/mo est. ?
105,381 km

Patriot Automotive Group

21550, Oakland MD

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Frequently Asked Questions

Our marketplace currently lists 11 used cars in Oakland, MD from dealers and private sellers. Prices range from $30,858 to $56,295.

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

The average listed price in Oakland, MD is $44,440. Browse by budget: under $10,000, under $20,000, or under $30,000.

No — you can buy from a seller in Oakland, MD 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 Maryland.