CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2020 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
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$32,147 • 65.9k miles • Certified
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • $350 Price Drop
  • Includes $492 Premium Upgrades
  • Below Average Mileage
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
2021 Toyota Highlander Limited AWD photo
2021 Toyota Highlander Limited AWD • Milwaukee, WI
Gold • 3.5L V6 Engine
$27,495 • 139.6k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Includes $886 Premium Upgrades
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander XLE FWD photo
Price Drop
2021 Toyota Highlander XLE FWD • Milwaukee, WI
Gray • 3.5L V6 Engine
$26,995 • 88.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $1,000 Price Drop
  • Fair Price - $212 Below Market
  • Motivation to Negotiate - High
More details
2021 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2021 Toyota Highlander Hybrid XLE AWD • West Allis, WI
Gray • 2.5L I4 Engine
$23,494 • 173.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $500 Price Drop
  • Good Price - $1,418 Below Market
  • Includes $556 Premium Upgrades
More details
2021 Toyota Highlander Hybrid Limited AWD photo
2021 Toyota Highlander Hybrid Limited AWD • West Allis, WI
Gray • 2.5L I4 Engine
$30,394 • 114.9k miles • Certified
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $703 Above Market
  • Includes $624 Premium Upgrades
  • Dealer Rating - 4.6 stars
More details
2021 Toyota Highlander Platinum AWD photo
Price Drop
2021 Toyota Highlander Platinum AWD • West Allis, WI
Gray • 3.5L V6 Engine
$30,394 • 90.9k miles • Certified
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $971 Price Drop
  • Great Price - $2,148 Below Market
  • Includes $440 Premium Upgrades
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
2021 Toyota Highlander XLE AWD photo
Price Drop
New Find
2021 Toyota Highlander XLE AWD • Milwaukee, WI
Red • 3.5L V6 Engine
$29,998 • 74.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $498 Price Drop
  • Fair Price - $68 Above Market
  • Average Mileage
More details
2021 Toyota Highlander LE AWD photo
Price Drop
New Find
2021 Toyota Highlander LE AWD • Milwaukee, WI
Silver • 3.5L V6 Engine
$26,748 • 84.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $144 Price Drop
  • Fair Price - $252 Above Market
  • Includes $390 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
New Find
2021 Toyota Highlander XLE AWD • Milwaukee, WI
Red • 3.5L V6 Engine
$31,749 • 49.4k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $240 Price Drop
  • Fair Price - $604 Below Market
  • Very Low Mileage
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
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Waukesha, WI
Gray • 3.5L V6 Engine
$29,299 • 87.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $360 Price Drop
  • Fair Price - $289 Above Market
  • Includes $459 Premium Upgrades
More details
2021 Toyota Highlander Platinum AWD photo
Price Drop
2021 Toyota Highlander Platinum AWD • Waukesha, WI
Gold • 3.5L V6 Engine
$29,449 • 107.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $449 Price Drop
  • Fair Price - $17 Above Market
  • CARFAX: One Owner
More details
2021 Toyota Highlander Platinum AWD photo
New Find
2021 Toyota Highlander Platinum AWD • Waukesha, WI
Red • 3.5L V6 Engine
$36,484 • 66.8k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Average Mileage
  • Dealer Rating - 4.5 stars
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
1-25 of 163 results

2020 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
35City MPG
35Hwy 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.