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1,314 listings
  • Price Drop
    $42,590
    great price
    $3,214 below market
    • 16,485 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana - Chicago (91 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Chicago, IL / 91 miles away from Middleton, WI

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH0RS554010
    Stock: 2003675350
    Certified Pre-Owned: No
    Listed since: 05-01-2025

  • Price Drop
    $38,590
    great price
    $3,169 below market
    • 29,929 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana - Chicago (91 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Chicago, IL / 91 miles away from Middleton, WI

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH9RS538275
    Stock: 2003582914
    Certified Pre-Owned: No
    Listed since: 03-17-2025

  • Price Drop
    $41,784
    great price
    $2,881 below market
    • 25,176 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Toyota of Brookfield (68 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Brookfield, WI / 68 miles away from Middleton, WI

    CARFAX One-Owner. Clean CARFAX. Certified. Midnight Black Metallic 2023 Toyota Highlander XSE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V ...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH5PS028517
    Stock: PRS2718
    Certified Pre-Owned: Yes
    Listed since: 05-15-2025

  • Price Drop
    $38,990
    great price
    $3,117 below market
    • 33,579 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana - Chicago (91 mi away)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Chicago, IL / 91 miles away from Middleton, WI

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH1RS532518
    Stock: 2003602020
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • $17,899
    great price
    $2,346 below market
    • 154,010 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Rosen Hyundai of Algonquin (89 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Algonquin, IL / 89 miles away from Middleton, WI

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH6JS896991
    Stock: Q38095A
    Certified Pre-Owned: No
    Listed since: 03-19-2025

  • Price Drop
    $38,590
    great price
    $2,596 below market
    • 34,147 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana - Chicago (91 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Chicago, IL / 91 miles away from Middleton, WI

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH1RS535774
    Stock: 2003511744
    Certified Pre-Owned: No
    Listed since: 02-25-2025

  • $42,054
    fair price
    $472 below market
    • 12,661 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Driveway (14 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Madison, WI / 14 miles away from Middleton, WI

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Sea...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH3PS025938
    Stock: PS025938K
    Certified Pre-Owned: No

  • $14,995
    great price
    $1,450 below market
    • 165,807 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Majeski Motors of Sterling (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    Close

    Located in Sterling, IL / 91 miles away from Middleton, WI

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH3HS436284
    Stock: 13069A
    Certified Pre-Owned: No
    Listed since: 02-08-2025

  • New Listing
    $34,998
    fair price
    $367 below market
    • 12,065 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • CarMax Kenosha (88 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Kenosha, WI / 88 miles away from Middleton, WI

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH4PS510252
    Stock: 27436425
    Certified Pre-Owned: No

  • Price Drop
    $13,480
    fair price
    $25 below market
    • 142,998 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Driveway (67 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Waukesha, WI / 67 miles away from Middleton, WI

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,V6 Cylinder Engine,5-Speed A/T,Power Door Loc...

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDZK3EH6DS095197
    Stock: SS3419752A
    Certified Pre-Owned: No

  • New Listing
    $20,879
    fair price
    $628 below market
    • 146,089 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Zeigler Toyota of Racine (84 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Mount Pleasant, WI / 84 miles away from Middleton, WI

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH9JS840804
    Stock: JS840804
    Certified Pre-Owned: No
    Listed since: 04-25-2025

  • New Listing
    $39,998
    fair price
    $780 above market
    • 15,657 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax Madison (4 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Madison, WI / 4 miles away from Middleton, WI

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH1MS537284
    Stock: 27410841
    Certified Pre-Owned: No

  • New Listing
    $37,979
    fair price
    $355 below market
    • 34,347 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (67 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Waukesha,, WI / 67 miles away from Middleton, WI

    CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepi...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH4NS567053
    Stock: NS567053A
    Certified Pre-Owned: No

  • Price Drop
    $28,654
    fair price
    $69 below market
    • 67,685 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • Umansky Toyota (80 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Milwaukee, WI / 80 miles away from Middleton, WI

    Command the road in this sleek and spacious 2019 Toyota Highlander XLE in bold Midnight Black Metallic with a matching black interior, available now a...

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH4KS928745
    Stock: 44721B
    Certified Pre-Owned: No
    Listed since: 04-26-2025

  • New Listing
    $17,000
    fair price
    $1,021 below market
    • 142,226 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Car Corral (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Kenosha, WI / 91 miles away from Middleton, WI

    Gorgeous 2015 Toyota Highlander Limited. This vehicle Runs and Drives Great. We just inspected and serviced this SUV with New Rear Brakes, and a New...

    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH1FS181824
    Stock: 9077
    Certified Pre-Owned: No
    Listed since: 02-08-2025

  • $50,433
    fair price
    $665 below market
    • 11,034 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Umansky Toyota (80 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Milwaukee, WI / 80 miles away from Middleton, WI

    Discover refined sophistication and advanced performance with the 2024 Toyota Highlander Platinum in Celestial Silver Metallic, available now at Umans...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH1RS561418
    Stock: T49503A
    Certified Pre-Owned: No
    Listed since: 05-12-2025

  • $37,022
    fair price
    $949 below market
    • 44,684 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Don Miller Chrysler Jeep Dodge Ram (5 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Madison, WI / 5 miles away from Middleton, WI

    Priced below KBB Fair Purchase Price! ***Blind Spot Monitoring***, ***Forward Collision Warning***, ***Adaptive Cruise Control***, ***Lane Departure W...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH2NS586605
    Stock: 255142A
    Certified Pre-Owned: No
    Listed since: 04-12-2025

  • $39,700
    fair price
    $1,295 above market
    • 32,692 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Driveway (75 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in West Allis, WI / 75 miles away from Middleton, WI

    CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Kee...

    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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH7RS533820
    Stock: G92475
    Certified Pre-Owned: No

  • New Listing
    $22,590
    good price
    $1,177 below market
    • 118,648 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 21 City / 29 Hwy MPG
    • Carvana - Chicago (91 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Chicago, IL / 91 miles away from Middleton, WI

    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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDZZRAH8MS031554
    Stock: 2003512276
    Certified Pre-Owned: No
    Listed since: 02-18-2025

  • Price Drop
    $37,107
    good price
    $1,655 below market
    • 50,283 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Umansky Toyota (80 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Milwaukee, WI / 80 miles away from Middleton, WI

    Elevate your family adventures with this stylish and versatile 2021 Toyota Highlander Limited in eye-catching Blizzard Pearl with a refined Graphite 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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH8MS121070
    Stock: T87081A
    Certified Pre-Owned: Yes
    Listed since: 04-28-2025

  • New Listing
    $34,997
    good price
    $1,908 below market
    • 34,602 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Zeigler Toyota of Racine (84 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Mount Pleasant, WI / 84 miles away from Middleton, WI

    One Owner - Clean History Report Showing No Accidents ++, Apple CarPlay + Android CarPlay ++, Pre-Collison Sys W/ Pedestrian Detection ++, Lane Depart...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH5MS160597
    Stock: MS160597
    Certified Pre-Owned: Yes
    Listed since: 05-05-2025

Showing 1 - 21 out of 1,314 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.