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New Toyota Highlander for Sale near Pittsfield, MA

102 results
Pittsfield, MA
2026 Toyota Highlander XLE AWD Lynch Toyota

2026 Toyota Highlander

New car | MSRP $47,243

$47,243

Manchester, CT
58 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
0
Stock number:
TT26360
VIN:
5TDKDRBH6TS50A304

Sponsored

2026 Toyota Highlander XLE AWD

2026 Toyota Highlander

New car | MSRP $48,102

$47,621

Manchester, CT
58 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
138
Stock number:
T26438
VIN:
5TDKDRBH5TS597040

Sponsored

2026 Toyota Highlander Platinum AWD

2026 Toyota Highlander

New car | MSRP $54,898

$54,898

Lancaster, MA
79 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Black Leather-Trimmed
Transmission:
8-Speed Dual Clutch
Mileage:
5
Stock number:
TL35548
VIN:
5TDKDRBH5TS599693

Sponsored

2026 Toyota Highlander XLE AWD

2026 Toyota Highlander

New car | MSRP $48,158

$45,158

Bristol, CT
55 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
3
Stock number:
NT261685
VIN:
5TDKDRBH9TS595940

2023 Toyota Highlander Platinum AWD

2023 Toyota Highlander

New car

$44,888

Cortlandt Manor, NY
88 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
Transmission:
Automatic
Mileage:
6,350
Stock number:
T123642
VIN:
5TDKDRBH1PS515522

2026 Toyota Highlander XLE AWD

2026 Toyota Highlander

New car | MSRP $49,681

$46,966

Bennington, VT
32 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Heavy Metal
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
0
Stock number:
T4922
VIN:
5TDKDRBH5TS598687

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $47,883

$47,883

Bristol, CT
55 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Wind Chill Prl
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
10
Stock number:
NT261720
VIN:
5TDKDRBH5TS599516

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $52,098

$51,577

Manchester, CT
58 mi away
Year:
2026
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)
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
0
Stock number:
T26296
VIN:
5TDKDRBH5TS600342

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $51,108

Negotiable

Wilbraham, MA
45 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
132
Stock number:
TS596094
VIN:
5TDKDRBH1TS596094

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $52,783

Negotiable

Norwich, CT
88 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Black Mixed Media-Trimmed
Transmission:
8-Speed Automatic
Mileage:
112
Stock number:
21014
VIN:
5TDKDRBH0TS598175

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car

$56,392

Manchester, NH
98 mi away
Year:
2026
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)
Fuel type:
Gasoline
Mileage:
3
Stock number:
TS599437
VIN:
5TDKDRBH9TS599437

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $49,322

$47,888

Glens Falls, NY
63 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Red (Ruby Flare Pearl [Extra_Cost_Color])
Fuel type:
Gasoline
Interior color:
Black Softex®-Trimmed [Softex]
Transmission:
8-Speed Dual Clutch
Mileage:
1
Stock number:
30063
VIN:
5TDKDRBH6TS600494

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $55,723

$55,223

Hartford, CT
55 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Heavy Metal
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
2
Stock number:
266003
VIN:
5TDKDRBH9TS599597

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $54,082

$50,448

Putnam, CT
79 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
265 hp 2.4L I4
Exterior color:
Blueprint
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
3
Stock number:
26164
VIN:
5TDKDRBH3TS595609

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $51,073

$51,073

Glens Falls, NY
63 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Wind Chill Pearl [Extra_Cost_Color]
Fuel type:
Gasoline
Interior color:
Black Mixed Media-Trimmed
Transmission:
8-Speed Dual Clutch
Mileage:
0
VIN:
5TDKDRBH9TS51A776

Preparing for a close up...

Photos coming soon

2025 Toyota Highlander

New car

Negotiable

Smithfield, RI
97 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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
35
Stock number:
251727X
VIN:
5TDKDRBHXSS593600

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $55,283

$55,283

Glens Falls, NY
63 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Wind Chill Pearl [Extra_Cost_Color]
Fuel type:
Gasoline
Interior color:
Black Leather-Trimmed
Transmission:
8-Speed Dual Clutch
Mileage:
0
VIN:
5TDKDRBH3TS51A739

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $51,258

$51,258

Manchester, CT
58 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
0
Stock number:
T26297
VIN:
5TDKDRBH7TS600939

Preparing for a close up...

Photos coming soon

2025 Toyota Highlander

New car | MSRP $48,028

$48,028

Westport, CT
91 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:
Magnetic Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
10
Stock number:
S552
VIN:
5TDKDRBH7SS594784

Preparing for a close up...

Photos coming soon

2025 Toyota Highlander

New car | MSRP $47,578

$47,578

Pittsfield, MA
0 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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
2
Stock number:
T51360
VIN:
5TDKDRBH9SS590848

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car

$52,848

Manchester, NH
98 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Red (Ruby Flare Pearl)
Fuel type:
Gasoline
Mileage:
8
Stock number:
TS596875
VIN:
5TDKDRBH7TS596875

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $47,243

$47,243

Manchester, CT
58 mi away
Year:
2026
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
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
0
Stock number:
TT26360
VIN:
5TDKDRBH6TS50A304

Preparing for a close up...

Photos coming soon

2026 Toyota Highlander

New car | MSRP $52,545

Negotiable

White River Junction, VT
95 mi away
Year:
2026
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Heavy Metal
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
0
Stock number:
50A581
VIN:
5TDKDRBHXTS50A581

  1. Home
  2. / New Cars
  3. / Toyota Highlander
  4. / Massachusetts
  5. / Pittsfield
Reviews
FAQs

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
Samuel B
5.0
Reviewed a 2023 Toyota Highlander on Oct 19, 2023

Extremely smooth ride and very comfortable seats. Love the interior layout.

Alexander H
4.0
Reviewed a 2023 Toyota XSE AWD on Aug 10, 2023

New 4cyl. is peppy enough, just seems out of place in a vehicle this size. That plus the buzzing of something so small compared to the V6 leaves much to be desired. Handling is great. With the xse sport tuned suspension...it drives relatively good. Only upside of going for the premium audio is the 12.3 inch infotainment. The jbl premium sound doesnt do it for me. Shallow sound and lackluster bass. Build quality is what youd expect from Toyota, surprising actually...in a good way. Seats are comfortable for those lucky to be in the 2 front rows. The third should be reserved for small children or average sized adults in a pinch. Cargo space is a bit small but its what to expect in this segment. The third row means some compromise in that dept. Overall, I love my new Highlander. Its definitely not without flaws but they are easy to look past.

Xexeed M
5.0
Reviewed a 2023 Toyota Highlander on May 04, 2023

Car’s 3rd row is not bumpy. Features like Birds Eye view are fantastic. Drives very smooth.

Anonymous
5.0
Reviewed a 2023 Toyota Limited FWD on Aug 30, 2024

It was a great value! Very few miles at a great price!

Anonymous
5.0
Reviewed a 2023 Toyota Highlander on Jun 28, 2024

The 2023 Highlander we purchased in June 2024 has performed very well. No complaints so far. It is quiet and smooth, and all the bells and whistles are pretty cool. We love it so far!

Toyota Highlander FAQs

What fuel types are available?

Gasoline engines are available.

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