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Used Toyota Highlander for Sale near Chester, MA

503 results
Chester, MA
2017 Toyota Highlander Limited AWD Watertown Mitsubishi

2017 Toyota Highlander

Limited AWD

78,713 miles

$22,791

Fair Deal
Watertown, CT
49 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Shoreline Blue Pearl
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Saddle Tan)
Mileage:
78,713
Stock number:
W2041
VIN:
5TDDZRFH2HS460195

Sponsored

2018 Toyota Highlander SE AWD

2018 Toyota Highlander

SE AWD

88,715 miles

$23,995

Fair Deal
Springfield, MA
23 mi away
Year:
2018
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:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
88,715
Stock number:
545898
VIN:
5TDJZRFH0JS545898

Sponsored

2018 Toyota Highlander XLE AWD

2018 Toyota Highlander

XLE AWD

80,931 miles

$23,995

Fair Deal
Springfield, MA
23 mi away
Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Brown
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
8-Speed Automatic
Mileage:
80,931
Stock number:
887453
VIN:
5TDJZRFH6JS887453

Sponsored

2025 Toyota Highlander LE FWD

2025 Toyota Highlander

LE FWD

20,275 miles

$38,597

Fair Deal
Store transfer to Hartford, CT
1,505 mi away • Price includes $1,599 shipping Price includes $1,599 shipping
Year:
2025
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Silver
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
20,275
Stock number:
28336496
VIN:
5TDKDRAH0SS550725

2023 Toyota Highlander LE AWD

2023 Toyota Highlander

LE AWD

31,321 miles

$31,475

Great Deal
Cheshire, MA
22 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
31,321
Stock number:
H26-203AM
VIN:
5TDKDRBH1PS002741

Preparing for a close up...

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2022 Toyota Highlander

XLE AWD

42,629 miles

$30,751

Great Deal
Cheshire, MA
22 mi away
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:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
42,629
Stock number:
H25-621AL
VIN:
5TDGZRBH9NS226392

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2021 Toyota Highlander

XSE AWD

83,815 miles

$29,100

Fair Deal
Bristol, CT
40 mi away
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:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
83,815
Stock number:
UA38102A
VIN:
5TDLZRBH8MS082086

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2023 Toyota Highlander

LE FWD

46,150 miles

$30,997

Fair Deal
Store transfer to Hartford, CT
2,442 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
46,150
Stock number:
28183012
VIN:
5TDKDRAHXPS002576

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2021 Toyota Highlander

Platinum AWD

56,343 miles

$34,998

Great Deal
Store transfer to Hartford, CT
111 mi away • Price includes $0 shipping Price includes $0 shipping
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:
Silver
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
56,343
Stock number:
28199591
VIN:
5TDFZRBH4MS063788

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Photos coming soon

2019 Toyota Highlander

XLE AWD

101,702 miles

$22,499

Good Deal
Bristol, CT
40 mi away
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:
White (Blizzard Pearl)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
101,702
Stock number:
UA0503P1
VIN:
5TDJZRFH8KS563535

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2023 Toyota Highlander

XLE AWD

49,905 miles

$31,994

Great Deal
Waterbury, CT
49 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
49,905
Stock number:
U10036
VIN:
5TDKDRBH1PS039112

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

14,541 miles

$39,923

Fair Deal
Hartford, CT
37 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
14,541
Stock number:
UP43118
VIN:
5TDKDRBH0PS033592

Sponsored

  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / Massachusetts
  5. / Chester
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander ## Summary - With 3,984 currently listed for sale and an **average price of $32,898**, 31.6% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2022 Toyota Highlander 4.58 / 5 stars. - **82.6% of 2022 Highlander models on CarGurus are accident-free**. - The 2022 Toyota Highlander provides tons of versatility, a stout V6 engine, and comes standard with essential safety features. ## Why it stands out The 2022 Toyota Highlander excels in delivering a balanced combination of comfort, safety, and performance, making it an ideal choice for families on the go. It features a spacious, three-row interior that offers impressive cargo capacity and utilizes clever storage solutions for ease of family life. The Highlander's robust V6 engine provides commendable power, while the standard suite of advanced safety technologies ensures peace of mind for drivers. Moreover, its versatility allows for various trims and optional features, making it a customizable option for differing needs and budgets. ## Other model years to consider - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,348 - Good/great deal percentage: 35.8% - User rating: 4.57 / 5 - Total listings: 2,215 - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-c32651)** - Average price: $35,174 - Good/great deal percentage: 33.0% - User rating: 4.36 / 5 - Total listings: 4,076 - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,649 - Good/great deal percentage: 35.0% - User rating: 4.76 / 5 - Total listings: 1,142 These recommendations are based on CarGurus' proprietary market data from March 20, 2026, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(691 reviews)

Customers say

Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.

AI generated from the text of customer reviews.

What people say

cargo space comfort interior performance safety
Julie W
5.0
Reviewed a 2021 Toyota Highlander on Jul 20, 2024

I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.

Melissa C
5.0
Reviewed a 2021 Toyota Highlander on May 05, 2024

Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.

Emmanuel S
5.0
Reviewed a 2022 Toyota Highlander on Apr 18, 2024

The car is great with very nice features. It is a good value in terms of price and nothing is missing. It is a good looking car

Anonymous
5.0
Reviewed a 2019 Toyota Highlander on Sep 03, 2024

great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort

James S
4.0
Reviewed a 2008 Toyota Highlander on Jul 16, 2024

We own 2 of these. One is the limited and the other is the all wheel drive. Over 150,000 on each and really just general maintenance issues so far with each. The clear coat is peeling and fading on the rear valance of each and the shocks and struts need to be replaced at this age. We have taken our limited everywhere including Texas, Colorado, North Carolina, Maryland, West Virginia, and more. Very good for families or dog owners and flexible with the third row seating. No major issues with either one so far!

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Chester, MA?

The average Toyota Highlander costs about $27,592.37. The average price has decreased by -4.1% since last year. The 503 for sale near Chester, MA on CarGurus, range from $3,228 to $56,998 in price.

How many Toyota Highlander vehicles in Chester, MA have no reported accidents or damage?

503 out of 503 for sale near Chester, MA have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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