Used 2021 Toyota Highlander for Sale near Connecticut

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200 vehicles found

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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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
87,367
Stock #:
X7803
VIN:
5TDGZRBH4LS027649
Magnetic Gray Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

Blasius South

Sponsored by Blasius South

2020 Toyota Highlander

XLE AWD

87,367 mi

Stratford, CT
46 mi away
Good Deal

$26,797

$25,797

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:
109,219
Stock #:
PB07330A
VIN:
5TDHZRBH6MS118332
Blueprint 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

Sponsored Listing

2021 Toyota Highlander

XLE AWD

109,219 mi

Plainville, CT
11 mi away
Good Deal
Third-party certified

$25,598

Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Moon Dust
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
101,086
Stock #:
AC260
VIN:
5TDGZRAH9LS015546
Moon Dust 2020 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2020 Toyota Highlander

XLE FWD

101,086 mi

Home delivery from Arab, AL
Price includes $1,364 shipping
Fair Deal

$25,762

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:
Celestial Silver Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
89,930
Stock #:
29142
VIN:
5TDCZRBHXMS530280
Celestial Silver Metallic 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

L AWD

89,930 mi

Home delivery from Cambridge, OH
Price includes $720 shipping
Great Deal

$23,297

Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
48,063
Stock #:
14798
VIN:
5TDGZRBH0NS257899
Gray 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2022 Toyota Highlander

XLE AWD

48,063 mi

Home delivery from Philadelphia, PA
Price includes $215 shipping
Great Deal

$32,929

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:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
50,924
Stock #:
4067
VIN:
5TDCZRBH5MS555894
Gray 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

L AWD

50,924 mi

Home delivery from East Rochester, NY
Price includes $458 shipping
Good Deal

$27,322

Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
Automatic
Mileage:
85,687
Stock #:
E-173398
VIN:
5TDHZRBH1NS173398
White 2022 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2022 Toyota Highlander

XLE AWD

85,687 mi

Home delivery from Bronx, NY
Price includes $106 shipping
Great Deal

$26,101

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:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
61,307
Stock #:
105756
VIN:
5TDGZRAH8MS057241
Black 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2021 Toyota Highlander

XLE FWD

61,307 mi

Home delivery from Avenel, NJ
Price includes $232 shipping
Great Deal

$25,982

CarGurus Analysis:

2021 Toyota Highlander

4.9

  • With 3,213 currently listed for sale and an average price of $30,037.00, 34.1% 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.

  • 77.3% 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:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,646
Stock #:
26019A
VIN:
5TDYZRAH3MS519080
Magnetic Gray Metallic 2021 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

Limited FWD

68,646 mi

Home delivery from Okatie, SC
Price includes $1,582 shipping
Fair Deal

$31,551

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:
57,230
Stock #:
SU109590
VIN:
5TDBZRBH9MS530959
Midnight Black Metallic 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

LE AWD

57,230 mi

Home delivery from Freehold, NJ
Price includes $202 shipping
Great Deal

$25,802

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:
Celestial Silver Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
40,092
Stock #:
OPT26099B
VIN:
5TDCZRBH3LS035241
Celestial Silver Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2020 Toyota Highlander

L AWD

40,092 mi

Home delivery from Wilmington, DE
Price includes $204 shipping
Good Deal

$28,610

Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
83,104
Stock #:
235440
VIN:
5TDBZRBH3NS235440
Gray 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2022 Toyota Highlander

LE AWD

83,104 mi

Home delivery from Newark, NJ
Price includes $129 shipping
Great Deal

$24,728

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:
Black
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
104,070
VIN:
5TDDZRBH6LS047405
Black 2020 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2020 Toyota Highlander

Limited AWD

104,070 mi

Waterbury, CT
26 mi away
Great Deal

$26,190

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:
Celestial Silver Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
63,765
Stock #:
6257
VIN:
5TDHZRBH5LS516257
Celestial Silver Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2020 Toyota Highlander

XLE AWD

63,765 mi

Home delivery from Little Ferry, NJ
Price includes $500 shipping
Great Deal

$28,294

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
23 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 3,213 currently listed for sale and an average price of $30,037.00, 34.1% 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.

  • 77.3% 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: $39,321.00
    • Good/great deal percentage: 34.6%
    • User rating: 5 / 5
    • Total listings: 3,433
  • 2023 Toyota Highlander

    • Average price: $35,671.00
    • Good/great deal percentage: 35.0%
    • User rating: 4.75 / 5
    • Total listings: 4,094
  • 2022 Toyota Highlander

    • Average price: $33,097.00
    • Good/great deal percentage: 35.1%
    • User rating: 4.5 / 5
    • Total listings: 4,514

This analysis is based on CarGurus' proprietary market data from August 10, 2026, CarGurus experts' opinions, and generative AI.

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