Used 2020 Toyota Highlander for Sale near Connecticut

Filters (3)

Location:

Only show listings in CT?

Include delivery listings?

241 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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
74,539
Stock #:
MU033739
VIN:
5TDGZRBH2LS033739
Moon Dust 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Key Hyundai of Milford

Sponsored by Key Hyundai of Milford

2020 Toyota Highlander

XLE AWD

74,539 mi

Milford, CT
44 mi away
Fair Deal

$29,496

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

Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
98,566
Stock #:
M18496A
VIN:
5TDBZRBH5LS518208
 2020 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

Sponsored Listing

2020 Toyota Highlander

LE AWD

98,566 mi

Danbury, CT
46 mi away
Fair Deal

$24,170

Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red (Burgundy)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,950
Stock #:
5485
VIN:
5TDBZRFH9KS965228
Red (Burgundy) 2019 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$4,000

 

2019 Toyota Highlander

LE Plus AWD

36,950 mi

Feeding Hills, MA
21 mi away
Great Deal

$30,394

$26,394

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:
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

CarGurus Analysis:

2020 Toyota Highlander

4.6

  • With 3,176 currently listed for sale and an average price of $27,993.00, 33.6% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it a 7.67 / 10.

  • 72.0% of 2020 Highlander models on CarGurus are accident free.

Research summarized using AI

Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
96,485
Stock #:
3640
VIN:
5TDBZRFHXKS953640
Silver 2019 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic

 

2019 Toyota Highlander

LE Plus AWD

96,485 mi

East Longmeadow, MA
22 mi away
Good Deal

$20,997

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

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:
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:
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

Sponsored Listing

2020 Toyota Highlander

XLE AWD

87,367 mi

Stratford, CT
46 mi away
Good Deal

$26,797

$25,797

CarGurus Analysis: 2020 Toyota Highlander

7.7
of 10
overall
Look and feel7/10
Technology7/10
Performance6/10
Safety9/10
Form & function9/10
Cost effectiveness8/10
Image Not Available

Summary

  • With 3,176 currently listed for sale and an average price of $27,993.00, 33.6% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it a 7.67 / 10.

  • 72.0% of 2020 Highlander models on CarGurus are accident free.

Why it stands out

The 2020 Toyota Highlander stands out by putting comfort ahead of flash. It was redesigned for 2020, and the result is a midsize three-row SUV that emphasizes silent operation, a soft ride, and a cosseting interior. The Highlander is described as the most comfortable midsize SUV, and its upper trims are said to feel and drive just like a Lexus, without the upcharge. That makes it appealing to buyers who want a family SUV that feels calm and upscale rather than exciting.

It also brings standard advanced safety features and a spacious cabin, two qualities that matter a lot in this segment. At the same time, the Highlander is not trying to win over drivers who value sharp responses or standout styling. Its handling is described as poor, and its styling as uninspired, so its strengths are clearly in comfort, space, and an easygoing character rather than driving enjoyment or visual drama.

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.

Read full review

A better way to discover your best deal

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