Skip to main content
Skip to Filters
1,100 listings
    • 29,539 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax Algonquin (89 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Algonquin, IL / 89 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: 5TDFZRBH0NS193570
    Stock: 26472545
    Certified Pre-Owned: No

  • New Listing
    $39,479
    fair price
    $205 above market
    • 37,200 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 8 Seats, 21 City / 28 Hwy MPG
    • Zeigler Toyota of Racine (84 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

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

    One Owner - Clean History Report Showing No Accidents ++, 18" Painted Alloy Wheels, 3rd row seats: split-bench, ABS brakes, Active Cruise Control, All...

    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: 5TDKDRBHXRS535836
    Stock: RS535836
    Certified Pre-Owned: Yes
    Listed since: 04-10-2025

  • $17,928
    fair price
    $442 above market
    • 143,982 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Bergstrom Chevrolet Buick GMC of Oshkosh (78 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Oshkosh, WI / 78 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH4FS142938
    Stock: 258462B
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • New Listing
    $34,440
    fair price
    $764 below market
    • 48,726 miles
    • 1 accident, 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 ++, 18" Machined Alloy Wheels, 3rd row seats: split-bench, Front Bucket Seats, Heated front seats, Power driver seat, Power Liftgate, Power ...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBH8MS554093
    Stock: MS554093
    Certified Pre-Owned: Yes
    Listed since: 05-06-2025

  • $35,971
    fair price
    $202 above market
    • 55,293 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Liberty Chrysler Jeep Dodge Ram (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Libertyville, IL / 99 miles away from Middleton, WI

    CARFAX One-Owner. Clean CARFAX. Blueprint 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC ***ONE OWNER***, ***CLEAN CARFAX***, AWD, AWD....

    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: 5TDGZRBH2NS175818
    Stock: 725878A
    Certified Pre-Owned: No
    Listed since: 05-23-2025

  • New Listing
    $36,854
    fair price
    $234 below market
    • 44,293 miles
    • 7 Seats, 20 City / 27 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. Celestial Silver Metallic 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD, Navigation System, Radio:...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH6NS169797
    Stock: PRS2727
    Certified Pre-Owned: No
    Listed since: 05-20-2025

    • 63,535 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • Umansky Toyota (80 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

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

    Experience modern versatility and bold style with the 2023 Toyota Highlander L, available now at Umansky Toyota in Milwaukee, Wisconsin. This striking...

    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: 5TDKDRAH9PS509470
    Stock: P09470
    Certified Pre-Owned: No
    Listed since: 04-23-2025

  • New Listing
    $14,956
    fair price
    $286 above market
    • 64,104 miles
    • 1 accident, 2 owners, personal use
    • 7 Seats, 17 City / 23 Hwy MPG
    • Liberty Chrysler Jeep Dodge Ram (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Leather Seats
    • Sunroof/Moonroof
    • Third-row seating
    Close

    Located in Libertyville, IL / 99 miles away from Middleton, WI

    Cypress Pearl 2010 Toyota Highlander SE AWD 5-Speed Automatic with Overdrive 3.5L V6 SMPI DOHC AWD, POWER SUNROOF, 3.5L V6 SMPI DOHC, AWD.If you're lo...

    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:

    19 Combined MPG (17 City/23 Highway)

    Listing Information:

    VIN: 5TDJK3EH3AS016240
    Stock: 7241485B
    Certified Pre-Owned: No
    Listed since: 05-26-2025

  • $33,777
    good price
    $698 below market
    • 44,466 miles
    • 2 accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 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

    Experience premium comfort and advanced technology with the 2020 Toyota Highlander Limited, featuring a sleek black exterior and refined black interio...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH1LS006342
    Stock: P06342
    Certified Pre-Owned: No
    Listed since: 03-12-2025

    • 37,557 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • CarMax Waukesha (68 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Waukesha, WI / 68 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: 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH9FS165647
    Stock: 26911358
    Certified Pre-Owned: No

  • $27,042
    fair price
    $28 above market
    • 73,593 miles
    • 1 accident, 1 owner, personal use
    • 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

    Elevate your driving experience with the 2019 Toyota Highlander XLE in bold Midnight Black Metallic, available now at Umansky Toyota in Milwaukee, Wis...

    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: 5TDJZRFH8KS956659
    Stock: 44757A
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • Stock photo**
    $39,995
    fair price
    $135 below market
    • 64,042 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • M'Lady Nissan (87 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Crystal Lake, IL / 87 miles away from Middleton, WI

    Delivers 27 Highway MPG and 20 City MPG! This Toyota Highlander boasts a Regular Unleaded V-6 3.5 L/211 engine powering this Automatic transmission. W...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDFZRBH2NS180593
    Stock: 50809A
    Certified Pre-Owned: No
    Listed since: 05-29-2025

  • New Listing
    $29,990
    fair price
    $425 above market
    • 58,871 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • Zeigler Toyota of Racine (84 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

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

    Pre-Collison Sys W/ Pedestrian Detection ++, Lane Departure Warning System ++, 18" Painted Alloy Wheels, 3rd row seats: split-bench, AM/FM radio: Siri...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDCZRBH0NS192311
    Stock: NS192311
    Certified Pre-Owned: Yes
    Listed since: 05-15-2025

  • New Listing
    • 138,710 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Lexus of Brookfield (69 mi away)
    • Five Star Dealer
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Brookfield, WI / 69 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: 5TDJZRFH3HS360433
    Stock: PJP2706A
    Certified Pre-Owned: No
    Listed since: 05-29-2025

    • 129,130 miles
    • No accidents, 4 owners, personal use
    • 5 Seats, 16 City / 21 Hwy MPG
    • Top Notch Auto Brokers (84 mi away)
    • AWD/4WD
    • Rear Bench Seats
    • Fold Flat Rear Seats
    • 3500lb Towing Capaci...
    Close

    Located in McHenry, IL / 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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: JTEHF21A030147908
    Stock: 25480
    Certified Pre-Owned: No

  • Price Drop
    • 37,475 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Zeigler Subaru of Kenosha (88 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

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

    2022 Toyota Highlander Platinum AWD, Bluetooth, Backup Camera, Navigation System, Lane Departure Warning System, Blind Spot Monitor, Android Auto, App...

    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: 5TDFZRBH4NS201315
    Stock: L16-3070A1
    Certified Pre-Owned: No
    Listed since: 05-16-2025

    • Not provided
    • 1 accident, 2 owners, personal use only
    • 7 Seats, 17 City / 22 Hwy MPG
    • Your Choice Autos - Waukegan (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Waukegan, IL / 99 miles away from Middleton, WI

    The 2012 Toyota Highlander Base AWD 4dr SUV offers a solid combination of features and practicality: Exterior: 17-inch alloy wheels Halogen headlights...

    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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 5TDBK3EH9CS132677
    Stock: WYC-132677
    Certified Pre-Owned: No
    Listed since: 02-05-2025

  • Stock photo**
    • 101,776 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Acura of Brookfield (70 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Brookfield, WI / 70 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: 5TDDZRFH7HS433543
    Stock: 25424
    Certified Pre-Owned: No
    Listed since: 05-09-2025

    • 130,241 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 20 City / 24 Hwy MPG
    • Your Choice Autos - Waukegan (99 mi away)
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Waukegan, IL / 99 miles away from Middleton, WI

    The 2017 Toyota Highlander LE 4dr SUV (2.7L I4) is a well-equipped, mid-size crossover SUV that combines a spacious interior, a smooth ride, and a goo...

    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/24 Highway)

    Listing Information:

    VIN: 5TDZARFH9HS027602
    Stock: WYC-027602
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • New Listing
    • 29,715 miles
    • 8 Seats, 20 City / 27 Hwy MPG
    • Toyota of Brookfield (68 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

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

    CARFAX One-Owner. Celestial Silver Metallic 2022 Toyota Highlander LE AWD 8-Speed Automatic 3.5L V6 DOHC AWD, 18" Painted Alloy Wheels, 3.003 Axle Rat...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDBZRBH1NS578084
    Stock: PML1368
    Certified Pre-Owned: No
    Listed since: 05-24-2025

    • 41,535 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 28 Hwy MPG
    • Majeski Motors of Sterling (91 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

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

    At Majeski Motors we now offer 4 great locations to serve you better than ever before in Sterling, Dixon, Rochelle and now Sycamore! With over 350 veh...

    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: 5TDKDRBH1PS003999
    Stock: 13321
    Certified Pre-Owned: No
    Listed since: 05-13-2025

Showing 43 - 63 out of 1,100 listings
Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius100 miles
Search radius

Make & Model

Year

New / Used

Price & Payments

Price Rating

Body Type

Trim

Mileage

Accidents & History

Engine & Drivetrain

Exterior Color

Interior Color

Total Seating

Edmunds Review

Features

Options & Packages

MPG

Listing Details


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