CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2019 Toyota Highlander for Sale in Milwaukee, WI

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2019 Toyota Highlander Hybrid Limited Platinum AWD photo
Price Drop
2019 Toyota Highlander Hybrid Limited Platinum AWD • Milwaukee, WI
Gray • 3.5L V6 Engine
$25,614 • 110.3k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $600 Price Drop
  • Good Price - $1,402 Below Market
  • Includes $144 Premium Upgrades
More details
2019 Toyota Highlander Limited AWD photo
2019 Toyota Highlander Limited AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$24,495 • 125.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $43 Above Market
  • Includes $144 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander Hybrid Limited AWD photo
Price Drop
2019 Toyota Highlander Hybrid Limited AWD • Milwaukee, WI
White • 3.5L V6 Engine
$28,998 • 88.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $1,000 Price Drop
  • Fair Price - $267 Above Market
  • Includes $161 Premium Upgrades
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD • Milwaukee, WI
Gold • 3.5L V6 Engine
$29,446 • 80.1k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Motivation to Negotiate - Increasing
  • Average Mileage
  • Dealer Rating - 4.3 stars
More details
2019 Toyota Highlander LE Plus AWD photo
Price Drop
2019 Toyota Highlander LE Plus AWD • Greenfield, WI
Black • 3.5L V6 Engine
$22,486 • 102.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $1,968 Price Drop
  • Fair Price - $225 Above Market
  • Includes $153 Premium Upgrades
More details
2019 Toyota Highlander Hybrid Limited Platinum AWD photo
Price Drop
New Find
2019 Toyota Highlander Hybrid Limited Platinum AWD • Milwaukee, WI
Red • 3.5L V6 Engine
$26,998 • 103.3k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $437 Price Drop
  • Good Price - $1,178 Below Market
  • Includes $533 Premium Upgrades
More details
2020 Toyota Highlander L AWD photo
New Find
2020 Toyota Highlander L AWD • Milwaukee, WI
White • 3.5L V6 Engine
$26,997 • 54.4k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $446 Above Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
2020 Toyota Highlander XLE AWD photo
New Find
2020 Toyota Highlander XLE AWD • Milwaukee, WI
White • 3.5L V6 Engine
$29,775 • 63.4k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $734 Above Market
  • Below Average Mileage
  • Dealer Rating - 4.4 stars
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Menomonee Falls, WI
Black • 3.5L V6 Engine
$17,854 • 159.3k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $640 Price Drop
  • Fair Price - $487 Below Market
  • Includes $411 Premium Upgrades
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD • Brookfield, WI
Gray • 3.5L V6 Engine
$27,132 • 78.7k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $687 Below Market
  • Average Mileage
  • Dealer Rating - 4.7 stars
More details
2020 Toyota Highlander Hybrid Platinum AWD photo
Price Drop
New Find
2020 Toyota Highlander Hybrid Platinum AWD • Brookfield, WI
Red • 2.5L I4 Engine
$27,811 • 135.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $421 Price Drop
  • Fair Price - $307 Above Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander LE Plus AWD photo
New Find
2019 Toyota Highlander LE Plus AWD • Waukesha, WI
Silver • 3.5L V6 Engine
$29,998 • 40.6k miles
•••

Not Ranked

CoPilot AI: It’s a “D+” Buy

  • Includes $189 Premium Upgrades
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2020 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2020 Toyota Highlander Hybrid XLE AWD • Waukesha, WI
Gray • 2.5L I4 Engine
$32,203 • 78.4k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • $202 Price Drop
  • Motivation to Negotiate - Increasing
  • Average Mileage
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Waukesha, WI
Red • 3.5L V6 Engine
$21,997 • 85.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • Great Price - $2,010 Below Market
  • Includes $548 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Waukesha, WI
Silver • 3.5L V6 Engine
$19,997 • 123.2k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $700 Price Drop
  • Good Price - $931 Below Market
  • Includes $127 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Waukesha, WI
Red • 3.5L V6 Engine
$26,997 • 50.8k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • Great Price - $1,933 Below Market
  • Includes $183 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD • Waukesha, WI
Brown • 3.5L V6 Engine
$28,494 • 63.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $496 Price Drop
  • Fair Price - $537 Below Market
  • Includes $171 Premium Upgrades
More details
2019 Toyota Highlander SE AWD photo
Price Drop
2019 Toyota Highlander SE AWD • Slinger, WI
Gray • 3.5L V6 Engine
$19,789 • 165.2k miles
•••

Not Ranked

CoPilot AI: It’s a “D-” Buy

  • Includes $399 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Mt Pleasant, WI
White • 3.5L V6 Engine
$20,286 • 141.4k miles • Certified
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $204 Price Drop
  • Good Price - $688 Below Market
  • Includes $131 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
New Find
2019 Toyota Highlander XLE AWD • Racine, WI
Black • 3.5L V6 Engine
$27,184 • 82.1k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Includes $166 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Hartford, WI
Gray • 3.5L V6 Engine
$21,995 • 113.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $1,000 Price Drop
  • Fair Price - $59 Above Market
  • Includes $130 Premium Upgrades
More details
2019 Toyota Highlander Limited Platinum AWD photo
Price Drop
2019 Toyota Highlander Limited Platinum AWD • West Bend, WI
Gray • 3.5L V6 Engine
$33,024 • 35.4k miles
•••

Not Ranked

CoPilot AI: It’s a “C+” Buy

  • $499 Price Drop
  • Includes $176 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander LE Plus AWD photo
2019 Toyota Highlander LE Plus AWD • West Bend, WI
White • 3.5L V6 Engine
$20,706 • 128.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $454 Above Market
  • Includes $137 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • West Bend, WI
Blue • 3.5L V6 Engine
$29,269 • 57.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $800 Above Market
  • Includes $650 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander SE AWD photo
New Find
2019 Toyota Highlander SE AWD • West Bend, WI
White • 3.5L V6 Engine
$29,705 • 52.1k miles
•••

Not Ranked

CoPilot AI: It’s a “C+” Buy

  • Includes $175 Premium Upgrades
  • Very Low Mileage
  • Dealer Rating - 4.6 stars
More details
1-25 of 131 results

2019 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
30City MPG
28Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like Highlander
Toyota Highlander near Milwaukee, WI
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.