Used Toyota Highlander for Sale near Pittsfield, MA

423 results

Pittsfield, MA

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2019 Toyota Highlander

XLE AWD

94,788 miles

$23,599

Good Deal

Groton, CT

96 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
Interior color:: Brown (Saddle Tan)
Transmission:: 8-Speed Automatic
Mileage:: 94,788
Stock number:: 6F03040
VIN:: 5TDJZRFH2KS582324

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2010 Toyota Highlander

SE 4WD

193,175 miles

$8,625

Fair Deal

Enfield, CT

47 mi away

Year:: 2010
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: Magnetic Gray Metallic
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 5-Speed Automatic Overdrive
Mileage:: 193,175
Stock number:: 130290A
VIN:: 5TDJK3EH8AS029694

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2023 Toyota Highlander

Platinum AWD

17,267 miles

$40,500

Great Deal

Latham, NY

34 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:: Magnetic Gray Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 17,267
Stock number:: 518748
VIN:: 5TDKDRBH9PS518748

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2022 Toyota Highlander

XLE AWD

42,629 miles

$30,751

Great Deal

Cheshire, MA

8 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

2024 Toyota Highlander

LE AWD

51,576 miles

$31,497

Good Deal

Store transfer to Albany, NY

1,664 mi away Price includes $1,499 shipping Price includes $1,499 shipping

Year:: 2024
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: White
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 51,576
Stock number:: 28159838
VIN:: 5TDKDRBH5RS537428

2025 Toyota Highlander

Platinum AWD

45,364 miles

$39,982

Great Deal

Framingham, MA

95 mi away

Year:: 2025
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
Transmission:: Automatic
Mileage:: 45,364
Stock number:: 11545
VIN:: 5TDKDRBH4SS575657

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2022 Toyota Highlander

XLE AWD

60,559 miles

$34,250

Fair Deal

Holyoke, MA

37 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:: White (Wind Chill Pearl)
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Gray (Graphite)
Transmission:: 8-Speed Automatic
Mileage:: 60,559
Stock number:: B7090A
VIN:: 5TDGZRBH3NS170773

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2023 Toyota Highlander

XLE AWD

23,303 miles

$37,995

Good Deal

Acton, MA

93 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:: 23,303
Stock number:: A26122C
VIN:: 5TDKDRBH7PS503925

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2022 Toyota Highlander

Limited AWD

28,031 miles

$38,290

Good Deal

Milford, CT

86 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:: White
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Brown (Harvest Beige)
Transmission:: 8-Speed Automatic
Mileage:: 28,031
Stock number:: MS089327A
VIN:: 5TDDZRBH4NS173846

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2021 Toyota Highlander

Limited AWD

32,543 miles

$35,075

Good Deal

Milford, CT

86 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:: Blueprint
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 32,543
Stock number:: M24676A
VIN:: 5TDDZRBH0MS098528

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2018 Toyota Highlander

XLE AWD

77,008 miles

$23,697

Good Deal

Acton, MA

93 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:: Gone
Transmission:: 8-Speed Automatic
Mileage:: 77,008
Stock number:: SA1579A
VIN:: 5TDJZRFH8JS558740

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2018 Toyota Highlander

LE Plus AWD

73,082 miles

$21,000

Great Deal

Johnston, RI

99 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:: Midnight Black Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 73,082
Stock number:: R6695A
VIN:: 5TDBZRFH1JS903367

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2021 Toyota Highlander

XLE AWD

53,106 miles

$29,998

Good Deal

Certified Pre-Owned

Fairfield, CT

90 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:: Black
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Transmission:: 8-Speed Automatic
Mileage:: 53,106
Stock number:: U7146A
VIN:: 5TDGZRBH1MS099619

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2023 Toyota Highlander

Limited AWD

41,742 miles

$38,388

Fair Deal

Kingston, NY

51 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
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Brown (Tan)
Transmission:: Automatic
Mileage:: 41,742
Stock number:: PS033757
VIN:: 5TDKDRBH6PS033757

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2021 Toyota Highlander

XLE AWD

89,139 miles

$28,999

Fair Deal

Hartford, CT

58 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:: White (Blizzard Pearl)
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 89,139
Stock number:: 4279
VIN:: 5TDGZRBH2MS119277

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2020 Toyota Highlander

XLE AWD

44,020 miles

$31,495

Fair Deal

Certified Pre-Owned

E Swanzey, NH

59 mi away

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:: Blue
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 44,020
Stock number:: 360313A
VIN:: 5TDHZRBH1LS018685

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2018 Toyota Highlander

XLE AWD

68,749 miles

$24,998

Fair Deal

Lowell, MA

97 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:: White
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 68,749
Stock number:: 25-124
VIN:: 5TDJZRFHXJS544970

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2015 Toyota Highlander

XLE

135,113 miles

$15,448

Good Deal

Manchester, NH

99 mi away

Year:: 2015
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: Blue
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 135,113
Stock number:: 15C139B
VIN:: 5TDJKRFH6FS102120

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2023 Toyota Highlander

Platinum AWD

42,725 miles

$40,500

Good Deal

Certified Pre-Owned

White River Junction, VT

95 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:: Glazed Caramel
Transmission:: 8-Speed Automatic
Mileage:: 42,725
Stock number:: PU3710A
VIN:: 5TDKDRBH8PS037339

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2019 Toyota Highlander

Limited Platinum AWD

105,744 miles

$26,597

Fair Deal

Store transfer to Albany, NY

1,499 mi away Price includes $1,599 shipping Price includes $1,599 shipping

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
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 105,744
Stock number:: 28209143
VIN:: 5TDDZRFH6KS950727

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2023 Toyota Highlander

Platinum AWD

30,907 miles

$40,936

Good Deal

Westbrook, CT

90 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
Interior color:: Black
Transmission:: Automatic
Mileage:: 30,907
Stock number:: 56928
VIN:: 5TDKDRBHXPS514546

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2017 Toyota Highlander

105,029 miles

$19,397

Fair Deal

Store transfer to Albany, NY

1,285 mi away Price includes $1,399 shipping Price includes $1,399 shipping

Year:: 2017
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Gray
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 105,029
Stock number:: 27982093
VIN:: 5TDZARFH2HS029675

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2022 Toyota Highlander

LE AWD

20,918 miles

$33,000

Good Deal

Chelmsford, MA

97 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:: White
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Le Awd
Transmission:: 8-Speed Automatic
Mileage:: 20,918
Stock number:: DNP006
VIN:: 5TDBZRBH2NS585934

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Overview

Reviews

FAQs

CarGurus recommends the 2022 Toyota Highlander

## Summary - With 3,898 currently listed for sale and an **average price of $33,089.00**, 30.5% 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 offers a spacious interior, powered by a stout V6 engine that delivers a smooth riding experience while including an extensive suite of standard safety features that buyers are looking for. ## Why it stands out The 2022 Toyota Highlander stands out in the competitive midsize SUV market by delivering a perfect blend of functionality, comfort, and cutting-edge safety features tailored for families. This three-row SUV is acclaimed for its spacious interiors and versatility, accommodating various configurations for passengers and cargo. Additionally, the Highlander boasts a powerful V6 engine, providing ample horsepower, while its user-friendly technology and standard advanced safety features are capable of enhancing the driving experience. Whether you're navigating daily commutes or family road trips, the Highlander's proven safety reputation and stylish design resonate well with a wide array of buyers. ## Other model years to consider - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,467.00 - Good/great deal percentage: 34.8% - User rating: 4.57 / 5 - Total listings: 2,166 - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-c32651)** - Average price: $35,417.00 - Good/great deal percentage: 31.6% - User rating: 4.36 / 5 - Total listings: 3,970 - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,730.00 - Good/great deal percentage: 34.2% - User rating: 4.76 / 5 - Total listings: 1,144 These recommendations are based on CarGurus' proprietary market data from March 23, 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 Pittsfield, MA?

The average Toyota Highlander costs about $27,683.80. The average price has decreased by -3.6% since last year. The 537 for sale near Pittsfield, MA on CarGurus, range from $3,235 to $56,998 in price.

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

537 out of 537 for sale near Pittsfield, MA have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.