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23 listings
  • New Listing
    $8,985
    fair price
    $202 above market
    • 40,089 miles
    • No accidents, 3 owners, personal use only
    • 34 City / 38 Hwy MPG
    • Jeff Wyler Toyota of Clarksville (89 mi away)
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Stability Control
    • Aux Audio Inputs
    Close

    Located in Clarksville, IN / 89 miles away from Winchester, KY

    Recent Arrival! ABS brakes, Alloy wheels, Electronic Stability Control, Exterior Appearance Package, Heated door mirrors, Illuminated entry, Low tire ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    36 Combined MPG (34 City/38 Highway)

    Listing Information:

    VIN: WMEEJ3BA8FK815040
    Stock: 31T15882A
    Certified Pre-Owned: No
    Listed since: 08-02-2025

  • $6,055
    fair price
    $169 above market
    • 85,817 miles
    • 1 accident, 10 owners, personal use only
    • 34 City / 38 Hwy MPG
    • Kings Toyota (90 mi away)
    • Tire Pressure Warnin...
    • Auto Climate Control
    • Stability Control
    • Post-collision safet...
    Close

    Located in Cincinnati, OH / 90 miles away from Winchester, KY

    34/38 City/Highway MPG Silver Metallic 2015 smart Fortwo Pure RWD 5 Speed Automatic with Smart-Shift 1.0L I3 Kings Toyota Certified Vehicle: Buy with ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    36 Combined MPG (34 City/38 Highway)

    Listing Information:

    VIN: WMEEJ3BA1FK801948
    Stock: FK801948
    Certified Pre-Owned: No
    Listed since: 06-28-2025

    • 44,709 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 3cyl automated manual
    • Mira Auto Sales (92 mi away)
    • Tire Pressure Warnin...
    • Auto Climate Control
    • Stability Control
    • Aux Audio Inputs
    • Soft Top
    Close

    Located in Cincinnati, OH / 92 miles away from Winchester, KY

    ***2009 SMART CAR***FORTWO***44,XXX MILES**** ***CONVERTIBLE***CLEAN TITLE***2 OWNERS** 1.0 L RWD 3 CYLINDER MOTOR, FUEL EFFICIENT WITH MANY OPTIONS...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    36 Combined MPG (33 City/41 Highway)

    Listing Information:

    VIN: WMEEK31X49K233671
    Stock: 233671
    Certified Pre-Owned: No
    Listed since: 03-02-2025

  • $5,391
    good price
    $577 below market
    • 113,718 miles
    • 1 accident, 4 owners, personal use
    • 33 City / 41 Hwy MPG
    • Prestige Motor Sales (93 mi away)
    • Tire Pressure Warnin...
    • Stability Control
    • Aux Audio Inputs
    • Post-collision safet...
    Close

    Located in Maineville, OH / 93 miles away from Winchester, KY

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    36 Combined MPG (33 City/41 Highway)

    Listing Information:

    VIN: WMEEJ31X59K237554
    Stock: 237554
    Certified Pre-Owned: No
    Listed since: 04-30-2025

  • New Listing
    • 3,479 miles
    • No accidents, 1 owner, personal use only
    • 34 City / 38 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to KY*
    • Tire Pressure Warnin...
    • Auto Climate Control
    • Stability Control
    • Post-collision safet...
    Close

    Located in Fresno, CA / 1,945 miles away from Winchester, KY

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    36 Combined MPG (34 City/38 Highway)

    Listing Information:

    VIN: WMEEJ3BA0FK806235
    Stock: 27422206
    Certified Pre-Owned: No

    • 18,642 miles
    • No accidents, 2 owners, personal use
    • 58 mi range
    • Kia Store Clarksville (89 mi away)
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    Close

    Located in Clarksville, IN / 89 miles away from Winchester, KY

    Recent Arrival! 2D CoupeRed 2018 smart Fortwo electric drive Passion RWDABS brakes, Alloy wheels, Electronic Stability Control, Heated door mirrors, I...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    Listing Information:

    VIN: WMEFJ9BAXJK328535
    Stock: C11547X
    Certified Pre-Owned: No
    Listed since: 07-25-2025

  • New Listing
    • 24,716 miles
    • No accidents, 2 owners, personal use only
    • 32 City / 39 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Heated seats
    • Leather Seats
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    Close

    Located in Charlotte, NC / 267 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA2GK055136
    Stock: 2003901531
    Certified Pre-Owned: No
    Listed since: 07-15-2025

  • New Listing
    • 40,002 miles
    • No accidents, 2 owners, personal use
    • Carvana (In-stock online)
    • Home delivery*
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Trip Computer
    Close

    Located in Dallas, TX / 794 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    Listing Information:

    VIN: WMEEJ9AA2FK836809
    Stock: 2003819030
    Certified Pre-Owned: No
    Listed since: 06-14-2025

  • New Listing
    • 34,778 miles
    • No accidents, 3 owners, personal use only
    • 32 City / 39 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NC to KY*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Charlotte, NC / 273 miles away from Winchester, KY

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA9GK107412
    Stock: 27144637
    Certified Pre-Owned: No

    • 39,604 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 58 mi range
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Dallas, TX / 794 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    Listing Information:

    VIN: WMEFJ9BA6HK237711
    Stock: 2003851140
    Certified Pre-Owned: No
    Listed since: 07-02-2025

  • New Listing
    • 34,016 miles
    • No accidents, 3 owners, personal use
    • 32 City / 39 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NV to KY*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Henderson, NV / 1,699 miles away from Winchester, KY

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA6GK068150
    Stock: 27398272
    Certified Pre-Owned: No

    • 41,322 miles
    • No accidents, 2 owners, personal use
    • 3cyl manual
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Alarm
    Close

    Located in Richmond, VA / 359 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    34 Combined MPG (31 City/38 Highway)

    Listing Information:

    VIN: WMEFK5DA8HK142862
    Stock: 2003850928
    Certified Pre-Owned: No
    Listed since: 07-09-2025

    • 36,893 miles
    • Issue reported, 4 owners, corporate fleet vehicle
    • Carvana (In-stock online)
    • Home delivery*
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Trip Computer
    Close

    Located in Portland, OR / 2,029 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Issue reported

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    Listing Information:

    VIN: WMEEJ9AA5FK839283
    Stock: 2003852592
    Certified Pre-Owned: No
    Listed since: 06-28-2025

    • 74,729 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • Carvana (In-stock online)
    • Home delivery*
    • Leather Seats
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    Close

    Located in Salt Lake City, UT / 1,484 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    Listing Information:

    VIN: WMEEJ9AAXEK732440
    Stock: 2003903207
    Certified Pre-Owned: No
    Listed since: 07-19-2025

    • 44,660 miles
    • No accidents, 2 owners, personal use
    • 32 City / 39 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Dallas, TX / 794 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA4GK068003
    Stock: 2003901386
    Certified Pre-Owned: No
    Listed since: 07-21-2025

  • New Listing
    • 51,311 miles
    • No accidents, 1 owner, personal use only
    • 32 City / 39 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Heated seats
    • Leather Seats
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    Close

    Located in Tampa, FL / 700 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA5GK055535
    Stock: 2003923240
    Certified Pre-Owned: No
    Listed since: 07-30-2025

  • New Listing
    • 53,039 miles
    • No accidents, 2 owners, personal use only
    • 31 City / 39 Hwy MPG, Manual
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Dallas, TX / 794 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    34 Combined MPG (31 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA2HK185743
    Stock: 2003649522
    Certified Pre-Owned: No
    Listed since: 04-17-2025

  • New Listing
    • 47,182 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 3cyl automated manual
    • CarMax (In-stock online)
    • Transfer available from TX to KY*
    • Leather Seats
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Stability Control
    Close

    Located in Houston, TX / 865 miles away from Winchester, KY

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    36 Combined MPG (34 City/38 Highway)

    Listing Information:

    VIN: WMEEK3BA3EK762470
    Stock: 27355126
    Certified Pre-Owned: No

  • Photos not available
    • 145,929 miles
    • No accidents, 5 owners, personal use only
    • 33 City / 41 Hwy MPG
    • Collins Auto Sales (25 mi away)
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    • USB Inputs
    • Auto Climate Control
    • Stability Control
    Close

    Located in Georgetown, KY / 25 miles away from Winchester, KY

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    36 Combined MPG (33 City/41 Highway)

    Listing Information:

    VIN: WMEEJ3BA4BK430195
    Stock: 5266
    Certified Pre-Owned: No
    Listed since: 07-26-2024

  • New Listing
    • 28,155 miles
    • 32 City / 39 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from VA to KY*
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    • Power Liftgate/Trunk
    • Auto Climate Control
    Close

    Located in Sterling, VA / 371 miles away from Winchester, KY

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    35 Combined MPG (32 City/39 Highway)

    Listing Information:

    VIN: WMEFJ5DA9GK053853
    Stock: 26528377
    Certified Pre-Owned: No

  • New Listing
    • 35,321 miles
    • 33 City / 41 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Sunroof/Moonroof
    • Tire Pressure Warnin...
    • Auto Climate Control
    • Stability Control
    • Aux Audio Inputs
    Close

    Located in Phoenix, AZ / 1,586 miles away from Winchester, KY

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    36 Combined MPG (33 City/41 Highway)

    Listing Information:

    VIN: WMEEJ3BA6AK368586
    Stock: 2003904125
    Certified Pre-Owned: No
    Listed since: 07-17-2025

Showing 1 - 21 out of 23 listings

Buying a smart fortwo in Winchester Kentucky

In Winchester, KY, where charming small-town living meets scenic landscapes, the smart fortwo stands out as a highly suitable choice for navigating the tight streets and parking in the bustling downtown area. With its compact size and nimble handling, this vehicle allows drivers to easily maneuver through busy intersections and find parking spots that larger cars would struggle to fit into. The quick acceleration at low speeds is particularly advantageous for darting in and out of traffic while heading to local farmers markets or enjoying the attractions at nearby parks.

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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.