Used Toyota Highlander for Sale in Winchester, KY

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$37,582
$37,582 above
$1,108/mo est. ?
53,377 km

Gates Ford Lincoln

Authorized EpicVIN dealer

40475, Richmond KY

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$16,995
$16,995 above
$501/mo est. ?
256,226 km

Gates Ford Lincoln

Authorized EpicVIN dealer

40475, Richmond KY

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$33,725
$33,725 above
$994/mo est. ?
68,011 km

Paul Miller Ford

Authorized EpicVIN dealer

4.4 Google 1663 reviews

40505, Lexington KY

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$12,686
$12,686 above
$374/mo est. ?
216,142 km

Dan Cummins Chrysler Dodge Jeep RAM

Authorized EpicVIN dealer

4.9 Google 1554 reviews

40361, Paris KY

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$6,701
$6,701 above
$198/mo est. ?
237,075 km

Toyota South

4.9 Google 1697 reviews

40475, Richmond KY

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$29,598
$29,598 above
$873/mo est. ?
143,646 km 3.5L

Georgetown Auto Sales

4.0
Star icon
7 reviews

40324, Georgetown KY

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$33,000
$33,000 above
$973/mo est. ?
146,621 km

40505, Lexington KY

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$27,686
$27,686 above
$816/mo est. ?
154,426 km

Dan Cummins of Georgetown

4.5 Google 295 reviews

40324, Georgetown KY

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$5,500
$5,500 above
$162/mo est. ?
329,792 km 3.5L

Auto Tronix

40505, Lexington KY

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$45,054
$45,054 above
$1,329/mo est. ?
39,551 km 2.5L

Toyota South

4.9 Google 1697 reviews

40475, Richmond KY

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$7,177
$7,177 above
$212/mo est. ?
365,903 km

Auto House of Lexington Inc

40505, Lexington KY

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$48,485
$48,485 above
$1,430/mo est. ?
39,863 km

Toyota South

4.9 Google 1697 reviews

40475, Richmond KY

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$33,686
$33,686 above
$993/mo est. ?
109,049 km

Dan Cummins Chevrolet Buick of Georgetown

40324, Georgetown KY

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$23,280
$23,280 above
$686/mo est. ?
167,959 km

Toyota South

4.9 Google 1697 reviews

40475, Richmond KY

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$44,292
$44,292 above
$1,306/mo est. ?
69,633 km

Toyota South

4.9 Google 1697 reviews

40475, Richmond KY

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$28,488
$28,488 above
$840/mo est. ?
85,165 km

Quantrell Auto Group

40509, Lexington KY

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$19,498
$19,498 above
$575/mo est. ?
239,608 km

Sutherland Chevrolet

40356, Nicholasville KY

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$12,200
$12,200 above
$360/mo est. ?
241,016 km

Toyota on Nicholasville

40356, Nicholasville KY

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$41,998
$41,998 above
$1,238/mo est. ?
73,083 km 2.5L

CarMax Lexington

40515, Lexington KY

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$19,990
$19,990 above
$589/mo est. ?
175,387 km

Auto House of Lexington Inc

40505, Lexington KY

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$22,997
$22,997 above
$678/mo est. ?
176,826 km

Ken's Autos

4.3 Google 68 reviews

40361, Paris KY

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$20,988
$20,988 above
$619/mo est. ?
202,592 km

Gates Nissan

40475, Richmond KY

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$34,602
$34,602 above
$1,020/mo est. ?
123,650 km 3.5L

Georgetown Auto Sales

4.0
Star icon
7 reviews

40324, Georgetown KY

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$28,687
$28,687 above
$846/mo est. ?
172,674 km

Toyota on Nicholasville

40356, Nicholasville KY

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Frequently Asked Questions

Our marketplace currently lists 119 used cars in Winchester, KY from dealers and private sellers. Prices range from $9,591 to $9,591.

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

The average listed price in Winchester, KY is $9,591. Browse by budget: under $10,000, under $20,000, or under $30,000.

No — you can buy from a seller in Winchester, KY 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 Kentucky.