Used 2021 Toyota Highlander for Sale nearWorcester, MA

Filters (3)

Location:

Only show listings in MA?

Include delivery listings?

294 vehicles found

Shop with transparent pricing.

Only show listings that include dealer fees
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
60,381
Stock #:
P8515
VIN:
5TDGZRBH4LS512695
Midnight Black Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Herb Connolly Chevrolet

Sponsored by Herb Connolly Chevrolet

2020 Toyota Highlander

XLE AWD

60,381 mi

Framingham, MA
20 mi away
Good Deal
Third-party certified

$30,693

CarGurus Analysis:

2021 Toyota Highlander

4.9

  • With 297 currently listed for sale near Worcester, MA and an average price of $28,546.00, 45.8% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 100.0% of 2021 Highlander models on CarGurus are accident free.

Research summarized using AI

Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
56,986
Stock #:
SU109590
VIN:
5TDBZRBH9MS530959
Midnight Black Metallic 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

LE AWD

56,986 mi

Home delivery from Freehold, NJ
Price includes $286 shipping
Great Deal

$26,386

Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blue
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Brown
Transmission:
Automatic
Mileage:
74,342
Stock #:
70076867
VIN:
5TDFZRAH0MS062610
Blue 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic
New arrival

 

2021 Toyota Highlander

Platinum FWD

74,342 mi

Store transfer to Westborough, MA
Price includes $1,299 shipping
Good Deal

$33,297

Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blueprint
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
61,659
Stock #:
C9844
VIN:
5TDDZRBH1MS112453
Blueprint 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
New arrival

Sponsored Listing

2021 Toyota Highlander

Limited AWD

61,659 mi

Westfield, MA
47 mi away
Fair Deal

$34,389

CarGurus Analysis: 2021 Toyota Highlander

7.5
of 10
overall
Look and feel8/10
Technology7/10
Performance6/10
Safety10/10
Form & function7/10
Cost effectiveness7/10
Image Not Available

Summary

  • With 297 currently listed for sale near Worcester, MA and an average price of $28,546.00, 45.8% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 100.0% of 2021 Highlander models on CarGurus are accident free.

Why it stands out

The 2021 Toyota Highlander stands out as a familiar three-row family SUV that leans heavily on comfort and safety. It already sits near the top of the sales charts for its segment, and the Highlander name carries strong recognition as it enters its 20th year of production. For 2021, Toyota adds additional safety-feature technology as standard equipment, reinforcing the Highlander’s appeal to buyers who want a practical family vehicle with a reassuring feature set.

Behind that straightforward mission, the Highlander’s strengths are easy to understand: it offers a great ride quality, a comfortable cabin, and plenty of space. Those qualities make it especially appealing for families who value everyday usability over flash. At the same time, it is not the most exciting choice in the class. Its styling is uninspired, the base engine is underwhelming, and its technology is described as outdated, so shoppers looking for the latest performance or infotainment polish may find it less compelling than its core virtues suggest.

Owner feedback generally reinforces that picture. Drivers commonly praise the 2021 Toyota Highlander for its comfort, reliability, smooth ride, high-quality interior, spaciousness, and safety features. Some, however, have been disappointed by fuel economy and by limited configurability for certain settings, including the third-row seating and lane assist functions.

Other model years to consider

  • 2024 Toyota Highlander

    • Average price: $39,767.00
    • Good/great deal percentage: 53.9%
    • User rating: 5 / 5
    • Total listings: 191
  • 2019 Toyota Highlander

    • Average price: $24,242.00
    • Good/great deal percentage: 37.2%
    • User rating: 4.76 / 5
    • Total listings: 312
  • 2016 Toyota Highlander

    • Average price: $17,730.00
    • Good/great deal percentage: 32.4%
    • User rating: 4.93 / 5
    • Total listings: 176

This analysis is based on CarGurus' proprietary market data from August 6, 2026, CarGurus experts' opinions, and generative AI.

Read full review

A better way to discover your best deal

Let us help you find a car you’ll love.