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4,881 listings
- $28,278great price$2,931 below market
- 79,744 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Deery Brothers Chevrolet (232 mi away)
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Located in Pleasant Hill, IA / 232 miles away from Madison, WI
Priced below KBB Fair Purchase Price! 18" Machined Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, Front Bucket Seats, Front Center Armres...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH6MS157935
Stock: 18400A
Certified Pre-Owned: No
Listed since: 06-18-2025 - Price Drop$32,999great price$3,723 below market
- 26,966 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Honda City Chicago (121 mi away)
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Located in Chicago, IL / 121 miles away from Madison, WI
2021 Toyota Highlander XLEPriced below KBB Fair Purchase Price! Odometer is 20903 miles below market average! 20/27 City/Highway MPGClean, one-owner 2...
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: 5TDHZRBH9MS155522
Stock: C20140A
Certified Pre-Owned: No
Listed since: 05-12-2025 - $33,080great price$3,323 below market
- 75,527 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Mungenast Burkard Alton Toyota (287 mi away)
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Located in Alton, IL / 287 miles away from Madison, WI
Clean CARFAX. Certified. TOYOTA GOLD CERTIFIED***7 YR/100K WARRANTY***BUY WITH CONFIDENCE, NAVIGATION, SUNROOF, 3RD ROW SEAT, LEATHER, NO ACCIDENT HIS...
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: 5TDDZRBH3MS101423
Stock: K4992
Certified Pre-Owned: Yes
Listed since: 06-27-2025 - Price Drop$28,598great price$3,297 below market
- 88,293 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Ed Martin Toyota (274 mi away)
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Located in Noblesville, IN / 274 miles away from Madison, WI
Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Gray, Graphite Artificial Leather.20/27 City/Highway MPGSeating for 8; 2nd Row...
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: 5TDHZRBH8MS094230
Stock: 6P9564
Certified Pre-Owned: Yes
Listed since: 07-09-2025 - $25,500great price$2,550 below market
- 103,751 miles
- 1 accident, 3 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Chrysler Dodge Jeep Ram of Columbia (320 mi away)
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Located in Columbia, MO / 320 miles away from Madison, WI
AWD, 3.003 Axle Ratio, 3rd row seats: split-bench, Alloy wheels, Apple CarPlay/Android Auto, Auto High-beam Headlights, Auto-dimming Rear-View mirror,...
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: 5TDGZRBH2MS530856
Stock: MS530856
Certified Pre-Owned: No
Listed since: 06-19-2025 - $30,794great price$3,161 below market
- 70,790 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Bob Rohrman Kia (224 mi away)
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Located in Lafayette, IN / 224 miles away from Madison, WI
AWD/4WD, Backup Camera, Bluetooth Handsfree, Local Trade, 112 POINT INSPECTION COMPLETED., Non-Smoker, *{Looking for great deal we got it!!!}, FULLY R...
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: 5TDJZRBH0MS060753
Stock: LK3078A
Certified Pre-Owned: No
Listed since: 05-20-2025 - $29,317great price$2,795 below market
- 115,400 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Kings Toyota (370 mi away)
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Located in Cincinnati, OH / 370 miles away from Madison, WI
CARFAX One-Owner. Navigation system: Dynamic Navigation (3-year trial). 20/27 City/Highway MPG Clean CARFAX. Ruby Flare Pearl 2021 Toyota Highlander P...
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: 5TDFZRBH4MS150333
Stock: MS150333
Certified Pre-Owned: No
Listed since: 05-30-2025 - Price Drop$28,495great price$3,532 below market
- 104,701 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Germain Ford of Columbus (383 mi away)
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Located in Columbus, OH / 383 miles away from Madison, WI
PANORAMIC SUNROOF, Backup Camera, Bluetooth, Automatic Headlights, Heated and Cooled Seats, Touch Screen, Navigation, 20" Painted Alloy Wheels. CARFAX...
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: 5TDFZRBH5MS145819
Stock: EA83503A
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$31,481great price$2,921 below market
- 66,022 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (288 mi away)
- Home delivery*
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Located in Ann Arbor, MI / 288 miles away from Madison, WI
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Navigatio...
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: 5TDJZRBH1MS121981
Stock: MS121981P
Certified Pre-Owned: No - $29,799good price$1,686 below market
- 79,847 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Seelye Kia Kalamazoo (198 mi away)
- Five Star Dealer
Close
Located in Kalamazoo, MI / 198 miles away from Madison, WI
CARFAX One-Owner.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Silver, All Weather Floor & Cargo Liner (TMS), Alloy wheels...
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: 5TDHZRBHXMS110041
Stock: 25K10186
Certified Pre-Owned: No
Listed since: 06-19-2025 - Price Drop$36,995good price$1,338 below market
- 45,463 miles
- No accidents, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarWise Gurnee (86 mi away)
Close
Located in Gurnee, IL / 86 miles away from Madison, WI
** Adaptive Cruise Control, ** Alloy Wheels / Premium Wheels, ** Automatic Emergency Braking, ** Backup Camera, ** Blind Spot Monitor, ** Bluetooth, H...
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: 5TDFZRBH2MS159564
Stock: GG29037
Certified Pre-Owned: No
Listed since: 06-17-2025 - $27,995good price$983 below market
- 95,213 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- A+ Auto Sales (367 mi away)
Close
Located in West Chester, OH / 367 miles away from Madison, WI
Recent Arrival! Gray 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC**New Tires**, Fresh Oil Change, Highlander XLE, 4D Sport Utility, 3...
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: 5TDGZRBH5MS547649
Stock: AT5841
Certified Pre-Owned: No
Listed since: 06-25-2025 - $38,330fair price$194 below market
- 68,628 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Sunshine Toyota (218 mi away)
Close
Located in Battle Creek, MI / 218 miles away from Madison, WI
LEATHER, HEATED SEATS, TOYOTA CERTIFIED VEHICLE, NAVIGATION, GREAT VEHICLE HISTORY, BLUETOOTH, BACK-UP CAMERA, BLIND SPOT MONITOR, USB PORT, AWD, 20" ...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH6MS102395
Stock: 21382
Certified Pre-Owned: Yes
Listed since: 06-19-2025 - Price Drop$25,399good price$1,861 below market
- 83,844 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Mike Miller Kia (156 mi away)
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Located in Peoria, IL / 156 miles away from Madison, WI
**ANOTHER MIKE MILLER 1-OWNER**, **LOCAL TRADE IN**, AWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Engine Immobilizer, L Grade Package....
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: 5TDCZRBH9MS534000
Stock: K080343A
Certified Pre-Owned: No
Listed since: 06-13-2025 - $34,993fair price$326 below market
- 63,932 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Minnesota Truck Headquarters of Brainerd (333 mi away)
Close
Located in Brainerd, MN / 333 miles away from Madison, WI
2021 Toyota Highlander XSE w/ Red Leather Interior / Moonroof 3.5L V6 DOHC AWD 8-Speed Automatic Blizzard Pearl w/ Red Leather Interior / Moonroof 4D ...
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: 5TDJZRBH0MS110941
Stock: BD05001R
Certified Pre-Owned: No
Listed since: 06-23-2025 - Price Drop$34,936good price$2,332 below market
- 82,129 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Sunshine Toyota (218 mi away)
Close
Located in Battle Creek, MI / 218 miles away from Madison, WI
LEATHER, HEATED SEATS, TOYOTA CERTIFIED VEHICLE, NAVIGATION, GREAT VEHICLE HISTORY, BLUETOOTH, BACK-UP CAMERA, BLIND SPOT MONITOR, USB PORT, TOYOTA CE...
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: 5TDFZRBH1MS083951
Stock: 21363
Certified Pre-Owned: Yes
Listed since: 06-05-2025 - Price Drop$32,543good price$1,632 below market
- 72,809 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Zeigler Buick GMC of Lincolnwood (112 mi away)
Close
Located in Lincolnwood, IL / 112 miles away from Madison, WI
2021 Toyota Highlander XSE Midnight Black Metallic AWD*, NAVIGATION w/BACKUP CAMERA*, BLUETOOTH w/MUSIC STREAMING*, BLIND SPOT MONITOR*, PRE-COLLSION ...
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: 5TDJZRBH3MS106026
Stock: M25401A
Certified Pre-Owned: No
Listed since: 05-23-2025 - $36,800fair price$578 below market
- 14,331 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Don Franklin Lexington Hyundai (435 mi away)
Close
Located in Lexington, KY / 435 miles away from Madison, WI
CARFAX One-Owner. Alloy wheels, AM/FM radio: SiriusXM, Apple CarPlay/Android Auto, Auto High-beam Headlights, Auto-dimming Rear-View mirror, Automatic...
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: 5TDGZRAH5MS522719
Stock: MS522719
Certified Pre-Owned: No
Listed since: 07-30-2025 - $39,900fair price$358 below market
- 14,477 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Twins Auto of Dublin (382 mi away)
Close
Located in Dublin, OH / 382 miles away from Madison, WI
YOU ALWAYS WIN AT TWINS OF DUBLIN.2021 Toyota Highlander XSE **NAVIGATION**, **USB PORTS**, **ALL WHEEL DRIVE**, **APPLE AND ANDROID PLAY**, **CLEANE...
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: 5TDLZRBH9MS112518
Stock: D4468
Certified Pre-Owned: No
Listed since: 06-12-2025 - $36,995fair price$1,218 below market
- 22,116 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Toyota Direct (394 mi away)
Close
Located in Columbus, OH / 394 miles away from Madison, WI
Moon Dust 2021 Toyota Highlander Limited FWD 8-Speed Automatic 3.5L V6 DOHC ONE OWNER!!, ***Clean AutoCheck***, LEATHER, Navigation system: Dynamic Na...
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: 5TDYZRAH9MS085392
Stock: MS085392A
Certified Pre-Owned: No
Listed since: 07-31-2025 - Price Drop$39,385fair price$621 below market
- 13,603 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Burnsville Toyota (226 mi away)
Close
Located in Burnsville, MN / 226 miles away from Madison, WI
*TOYOTA CERTIFIED*, *CRUISE CONTROL*, *HEATED FRONT SEATS*, LEATHER SEATS*, BACKUP CAMERA*, MOONROOF*, ALLOY WHEELS*, BLUETOOTH*, Highlander XLE, 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: 5TDGZRBHXMS554645
Stock: 1036040
Certified Pre-Owned: Yes
Listed since: 04-24-2025
Showing 1 - 21 out of 4,881 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2021 Toyota Highlander in Madison, WI Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $28,223 | $30,284 | $32,350 |
| Clean | $27,623 | $29,624 | $31,629 |
| Average | $26,621 | $28,524 | $30,427 |
| Rough | $25,319 | $27,094 | $28,864 |
The average list price of a used 2021 Toyota Highlander in Madison, Wisconsin is $32,505. The average mileage on a used Toyota Highlander 2021 for sale in Madison, Wisconsin is 66,076. Based on the average mileage of 66,076 for used 2021 Toyota Highlander for sale in Madison, WI and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Toyota Highlander 2021 in Madison, Wisconsin to be $26,621.
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