CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used Toyota Highlander for Sale in Milwaukee, WI

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2023 Toyota Highlander L FWD photo
2023 Toyota Highlander L FWD • West Allis, WI
Gray • 2.4L I4 Engine
$34,995 • 11.3k miles • Certified
•••

#277 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.6 stars
More details
2018 Toyota Highlander XLE FWD photo
2018 Toyota Highlander XLE FWD • Chicago, IL
Silver • 3.5L V6 Engine
$19,995 • 153k miles
•••

#296 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.0 stars
More details
2017 Toyota Highlander XLE AWD photo
2017 Toyota Highlander XLE AWD • Sheboygan, WI
Gray • 3.5L V6 Engine
$16,700 • 153.3k miles
•••

#180 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $113 Above Market
  • Dealer Rating - 4.8 stars
More details
2016 Toyota Highlander Limited Platinum AWD photo
2016 Toyota Highlander Limited Platinum AWD • Schaumburg, IL
White • 3.5L V6 Engine
$23,400 • 82k miles
•••

#221 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2015 Toyota Highlander XLE AWD photo
Price Drop
2015 Toyota Highlander XLE AWD • Madison, WI
Silver • 3.5L V6 Engine
$13,883 • 188.2k miles
•••

#239 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $109 Price Drop
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.6 stars
More details
2018 Toyota Highlander XLE AWD photo
22
Price Drop
2018 Toyota Highlander XLE AWD • Chicago, IL
Gray • 3.5L V6 Engine
$22,200 • 73.9k miles
•••

#22 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $200 Price Drop
  • Great Price - $2,240 Below Market
  • Includes $145 Premium Upgrades
More details
2020 Toyota Highlander Hybrid XLE AWD photo
2020 Toyota Highlander Hybrid XLE AWD • McHenry, IL
Gray • 2.5L I4 Engine
$28,999 • 101.7k miles
•••

#259 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.7 stars
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD • Palos Hills, IL
Blue • 3.5L V6 Engine
$24,995 • 107.2k miles
•••

#30 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,957 Below Market
  • Includes $641 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Oshkosh, WI
Silver • 3.5L V6 Engine
$24,388 • 87.6k miles
•••

#192 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $268 Above Market
  • Includes $152 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Muskego, WI
3.5L V6 Engine
$26,999 • 95.2k miles
•••

#188 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1,000 Price Drop
  • Fair Price - $203 Above Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Stone Park, IL
Gray • 3.5L V6 Engine
$25,750 • 83.4k miles
•••

#255 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $200 Price Drop
  • Includes $155 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2019 Toyota Highlander XLE FWD photo
Price Drop
2019 Toyota Highlander XLE FWD • Elgin, IL
Red • 3.5L V6 Engine
$19,999 • 114k miles
•••

#62 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $1,000 Price Drop
  • Good Price - $969 Below Market
  • Includes $694 Premium Upgrades
More details
2023 Toyota Highlander LE FWD photo
Price Drop
2023 Toyota Highlander LE FWD • Gurnee, IL
White • 2.4L I4 Engine
$26,395 • 62.8k miles
•••

#72 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $150 Price Drop
  • Good Price - $1,386 Below Market
  • CARFAX: One Owner
More details
2022 Toyota Highlander Hybrid XLE AWD photo
2022 Toyota Highlander Hybrid XLE AWD • Holland, MI
Gray • 2.5L I4 Engine
$37,499 • 54k miles
•••

#264 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Below Average Mileage
  • Dealer Rating - 4.4 stars
More details
2023 Toyota Highlander Limited FWD photo
9
Price Drop
2023 Toyota Highlander Limited FWD • Glendale, WI
Green • 2.4L I4 Engine
$33,576 • 53.1k miles
•••

#9 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1 Price Drop
  • Great Price - $3,144 Below Market
  • CARFAX: One Owner
More details
2016 Toyota Highlander XLE AWD photo
17
Price Drop
2016 Toyota Highlander XLE AWD • Crestwood, IL
White • 3.5L V6 Engine
$14,994 • 139.4k miles
•••

#17 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $505 Price Drop
  • Great Price - $2,500 Below Market
  • Includes $337 Premium Upgrades
More details
2021 Toyota Highlander LE AWD photo
Price Drop
2021 Toyota Highlander LE AWD • Madison, WI
Blue • 3.5L V6 Engine
$21,990 • 104.9k miles
•••

#73 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,260 Below Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Cedarburg, WI
Gray • 3.5L V6 Engine
$16,371 • 160.5k miles
•••

#79 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $529 Price Drop
  • Good Price - $1,034 Below Market
  • Includes $104 Premium Upgrades
More details
2021 Toyota Highlander Hybrid Limited AWD photo
2021 Toyota Highlander Hybrid Limited AWD • Wauwatosa, WI
White • 2.5L I4 Engine
$28,994 • 114.6k miles
•••

#29 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,965 Below Market
  • Includes $582 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD • Sauk City, WI
White • 3.5L V6 Engine
$26,750 • 88.4k miles
•••

#210 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $247 Price Drop
  • Fair Price - $657 Above Market
  • Average Mileage
More details
2023 Toyota Highlander LE AWD photo
2023 Toyota Highlander LE AWD • Holland, MI
Black • 2.4L I4 Engine
$32,916 • 57.4k miles
•••

#269 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D” Buy

  • Dealer Rating - 4.1 stars
More details
2017 Toyota Highlander XLE AWD photo
2017 Toyota Highlander XLE AWD • Westmont, IL
Black • 3.5L V6 Engine
$25,500 • 51.6k miles
•••

#64 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $882 Below Market
  • Includes $601 Premium Upgrades
  • Very Low Mileage
More details
2015 Toyota Highlander XLE AWD photo
3
2015 Toyota Highlander XLE AWD • Milwaukee, WI
3.5L V6 Engine
$17,876 • 106.5k miles
•••

#3 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $4,287 Below Market
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Kenosha, WI
White • 3.5L V6 Engine
$29,300 • 42.9k miles
•••

#118 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $300 Price Drop
  • Fair Price - $432 Above Market
  • Includes $179 Premium Upgrades
More details
2020 Toyota Highlander Limited AWD photo
Price Drop
2020 Toyota Highlander Limited AWD • Green Bay, WI
Blue • 3.5L V6 Engine
$25,990 • 130k miles
•••

#272 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • $3,000 Price Drop
  • Includes $529 Premium Upgrades
  • CARFAX: One Owner
More details
1-25 of 417 results
HomeToyotaHighlander

2025 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
35City MPG
35Hwy MPG
NHTSA Rating Summary
Dimensions
Toyota Highlander for Sale by City
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.