Used Toyota Highlander for Sale in Winchester, VA

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$5,815
$5,815 above
$171/mo est. ?
280,310 km 3.0L

Purcellville Motors

Authorized EpicVIN dealer

5.0
Star icon
1 review
4.4 Google 48 reviews

20132, Purcellville VA

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$17,797
$17,797 above
$525/mo est. ?
273,251 km

Malloy Toyota

Authorized EpicVIN dealer

22601, Winchester VA

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$32,897
$32,897 above
$970/mo est. ?
164,447 km

Malloy Toyota

Authorized EpicVIN dealer

22601, Winchester VA

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$42,997
$42,997 above
$1,268/mo est. ?
39,244 km 2.4L

Malloy Toyota

Authorized EpicVIN dealer

22601, Winchester VA

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$22,897
$22,897 above
$675/mo est. ?
161,621 km

Malloy Toyota

22601, Winchester VA

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241,401 km 3.3L

Bobby's Used Cars - Charles Town

25414, Charles Town WV

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$6,995
$6,995 above
$206/mo est. ?
415,400 km

Valley Used Cars Inc

25438, Ranson WV

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$32,499
$32,499 above
$958/mo est. ?
156,893 km

Honeycar

22602, Winchester VA

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$15,500
$15,500 above
$457/mo est. ?
208,018 km 3.5L

Lewin Yount Auto Sales

22602, Winchester VA

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278,448 km

25403, Martinsburg WV

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$30,900
$30,900 above
$911/mo est. ?
66,269 km

CMA's Toyota of Martinsburg

25401, Martinsburg WV

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$37,897
$37,897 above
$1,118/mo est. ?
56,942 km

Malloy Toyota

22601, Winchester VA

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$35,998
$35,998 above
$1,062/mo est. ?
68,791 km

CarMax Winchester

22601, Winchester VA

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$37,688
$37,688 above
$1,111/mo est. ?
51,753 km

CMA's Honda of Winchester

4.7 Google 1451 reviews

22602, Winchester VA

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$24,699
$24,699 above
$728/mo est. ?
161,631 km

Honeycar

22602, Winchester VA

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$18,000
$18,000 above
$531/mo est. ?
246,153 km

Safford Chrysler Jeep Dodge Ram FIAT of Winchester

2.3
Star icon
4 reviews

22601, Winchester VA

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$10,977
$10,977 above
$324/mo est. ?
235,089 km

Elite Auto Sales Inc

22630, Front Royal VA

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$11,877
$11,877 above
$350/mo est. ?
290,140 km

Elite Auto Sales Inc

22630, Front Royal VA

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$31,850
$31,850 above
$939/mo est. ?
82,372 km

Cma's Chrysler Dodge Jeep Ram

25401, Martinsburg WV

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$11,995
$11,995 above
$354/mo est. ?
226,499 km

Lewin Yount Auto Sales

22602, Winchester VA

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$27,550
$27,550 above
$812/mo est. ?
173,493 km

Parsons Kia

22601, Winchester VA

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287,159 km

CMA's Chevrolet of Martinsburg and CMA's Toyota of Martinsburg

25401, Martinsburg WV

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$31,495
$31,495 above
$929/mo est. ?
71,188 km

22602, Winchester VA

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$4,999
$4,999 above
$147/mo est. ?
321,184 km

Peru Autos Export

22602, Winchester VA

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Frequently Asked Questions

Our marketplace currently lists 26 used cars in Winchester, VA from dealers and private sellers. Prices range from $4,587 to $42,951.

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

The average listed price in Winchester, VA is $26,104. 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.