CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2020 Toyota Highlander for Sale in Boston, MA

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2020 Toyota Highlander LE AWD photo
Price Drop
2020 Toyota Highlander LE AWD Lynn, MA
Silver 3.5L V6 Engine
$19,794 133.2k miles
•••

#42 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $1,300 Price Drop
  • Good Price - $887 Below Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD Danvers, MA
Gray 3.5L V6 Engine
$25,988 93.4k miles
•••

#123 2019-2021 Toyota Highlander

CoPilot AI: It’s aD+” Buy

  • $662 Price Drop
  • Includes $146 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Toyota Highlander Hybrid XLE AWD photo
2021 Toyota Highlander Hybrid XLE AWD Danvers, MA
Silver 2.5L I4 Engine
$33,997 53.8k miles
•••

#109 2019-2021 Toyota Highlander

CoPilot AI: It’s aC-” Buy

  • Very Low Mileage
  • Dealer Rating - 4.4 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD Warwick, RI
White 3.5L V6 Engine
$23,995
•••
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD Abington, MA
White 3.5L V6 Engine
$29,210 51.8k miles
•••

#63 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Fair Price - $143 Above Market
  • Very Low Mileage
  • Dealer Rating - 4.0 stars
More details
2020 Toyota Highlander Hybrid XLE AWD photo
2020 Toyota Highlander Hybrid XLE AWD Greenfield, MA
White 2.5L I4 Engine
$30,549 72.2k miles
•••

#92 2019-2021 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $298 Above Market
  • Motivation to Negotiate - Increasing
  • Below Average Mileage
More details
2021 Toyota Highlander Limited AWD photo
2021 Toyota Highlander Limited AWD Worcester, MA
White 3.5L V6 Engine
$33,953 60.8k miles Certified
•••

#146 2019-2021 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • CARFAX: One Owner
  • Below Average Mileage
  • Dealer Rating - 4.6 stars
More details
2021 Toyota Highlander Hybrid XLE AWD photo
2021 Toyota Highlander Hybrid XLE AWD Nashua, NH
White 2.5L I4 Engine
$32,988 51.6k miles
•••

#49 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Fair Price - $479 Below Market
  • Very Low Mileage
  • Dealer Rating - 4.9 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD Marlboro, MA
Black 3.5L V6 Engine
$24,999 86k miles
•••

#89 2019-2021 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $138 Above Market
  • Includes $480 Premium Upgrades
  • Below Average Mileage
More details
2019 Toyota Highlander SE AWD photo
2019 Toyota Highlander SE AWD Auburn, MA
Black 3.5L V6 Engine
$34,537 45.8k miles
•••

#137 2019-2021 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • Includes $178 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Very Low Mileage
More details
2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD Norwood, MA
Silver 3.5L V6 Engine
$25,600 76.9k miles
•••

#29 2019-2021 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $200 Price Drop
  • Good Price - $1,113 Below Market
  • Includes $156 Premium Upgrades
More details
2020 Toyota Highlander Limited AWD photo
Price Drop
2020 Toyota Highlander Limited AWD Watertown, MA
White 3.5L V6 Engine
$33,971 29.8k miles
•••

#113 2019-2021 Toyota Highlander

CoPilot AI: It’s aC-” Buy

  • $913 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander LE AWD photo
23
Price Drop
2021 Toyota Highlander LE AWD Boston, MA
Silver 3.5L V6 Engine
$27,991 37.3k miles
•••

#23 2019-2021 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $298 Price Drop
  • Good Price - $1,487 Below Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander LE AWD photo
2019 Toyota Highlander LE AWD Boston, MA
Red 3.5L V6 Engine
$25,998 99.2k miles
•••

#150 2019-2021 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • Includes $163 Premium Upgrades
  • Average Mileage
  • Dealer Rating - 4.6 stars
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD Kingston, MA
Gray 3.5L V6 Engine
$30,998 67.8k miles Certified
•••

#130 2019-2021 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • Includes $389 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Below Average Mileage
More details
2020 Toyota Highlander XLE AWD photo
Price Drop
2020 Toyota Highlander XLE AWD Swanzey, NH
Gray 3.5L V6 Engine
$25,995 104.1k miles
•••

#84 2019-2021 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $1,000 Price Drop
  • Fair Price - $22 Below Market
  • CARFAX: One Owner
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD Coventry, RI
Black 3.5L V6 Engine
$29,900 62.6k miles
•••

#74 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Fair Price - $799 Above Market
  • Includes $708 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD Raynham, MA
White 3.5L V6 Engine
$20,295 119.7k miles
•••

#82 2019-2021 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $180 Below Market
  • Includes $128 Premium Upgrades
  • Dealer Rating - 4.8 stars
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD Nashua, NH
Red 3.5L V6 Engine
$30,750 52.1k miles
•••

#54 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $250 Price Drop
  • Fair Price - $236 Below Market
  • Motivation to Negotiate - Increasing
More details
2020 Toyota Highlander XLE AWD photo
Price Drop
2020 Toyota Highlander XLE AWD Concord, NH
Black 3.5L V6 Engine
$29,487 65k miles
•••

#111 2019-2021 Toyota Highlander

CoPilot AI: It’s aC-” Buy

  • $500 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
7
2019 Toyota Highlander XLE AWD Nashua, NH
Blue 3.5L V6 Engine
$26,570 51.8k miles
•••

#7 2019-2021 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $3,000 Below Market
  • Includes $187 Premium Upgrades
  • Very Low Mileage
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD Dedham, MA
Black 3.5L V6 Engine
$19,900 120.7k miles
•••

#96 2019-2021 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $500 Price Drop
  • Fair Price - $374 Above Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander LE AWD photo
1
2019 Toyota Highlander LE AWD Londonderry, NH
Gray 3.5L V6 Engine
$19,995 100k miles
•••

#1 2019-2021 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $5,643 Below Market
  • Includes $162 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD Laconia, NH
Silver 3.5L V6 Engine
$25,740 84.4k miles
•••

#36 2019-2021 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Good Price - $1,588 Below Market
  • Average Mileage
  • Dealer Rating - 4.7 stars
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD Tewksbury, MA
Black 3.5L V6 Engine
$30,900 89k miles
•••

#131 2019-2021 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • Includes $655 Premium Upgrades
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.7 stars
More details
1-25 of 188 results

2020 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
36City MPG
35Hwy MPG
NHTSA Rating Summary
Dimensions
Most Popular Models like Highlander
Toyota Highlander near Boston, MA
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.