Certified Toyota Highlander for Sale nearMiddlebury, CT
12 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Cockpit Red
- Transmission:
- Automatic
- Mileage:
- 49,282
- Stock #:
- U33414
- VIN:
- 5TDKDRBH1PS526214
Sponsored by Riverhead Toyota
2023 Toyota Highlander
XSE AWD
49,282 mi
Riverhead, NY
47 mi away
Fair Deal
$37,920
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,893
- Stock #:
- UP43719
- VIN:
- 5TDKDRBH0SS579284
New arrival
Sponsored Listing
2025 Toyota Highlander
XLE AWD
24,893 mi
Hartford, CT
30 mi away
Fair Deal
$44,594
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,034
- Stock #:
- P5411
- VIN:
- 5TDKDRBH8TS609388
New arrival
Sponsored Listing
2026 Toyota Highlander
XSE AWD
6,034 mi
Wallingford, CT
16 mi away
Good Deal
$49,424
- 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:
- 47,725
- Stock #:
- N7077A
- VIN:
- 5TDJZRBH0MS076595
2021 Toyota Highlander
XSE AWD
47,725 mi
Cheshire, CT
12 mi away
Good Deal
$33,473
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 86,715
- Stock #:
- 627362A
- VIN:
- 5TDLZRBH0NS244486
2022 Toyota Highlander
XSE AWD
86,715 mi
Wappingers Falls, NY
41 mi away
Good Deal
$30,692
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,893
- Stock #:
- UP43719
- VIN:
- 5TDKDRBH0SS579284
New arrival
2025 Toyota Highlander
XLE AWD
24,893 mi
Hartford, CT
30 mi away
Fair Deal
$44,594
- 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:
- Cockpit Red
- Transmission:
- Automatic
- Mileage:
- 49,282
- Stock #:
- U33414
- VIN:
- 5TDKDRBH1PS526214
2023 Toyota Highlander
XSE AWD
49,282 mi
Riverhead, NY
47 mi away
Fair Deal
$37,920
- 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:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,242
- Stock #:
- 625313A
- VIN:
- 5TDJZRFH2KS600353
2019 Toyota Highlander
SE AWD
97,242 mi
Wappingers Falls, NY
41 mi away
Good Deal
$23,991
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,034
- Stock #:
- P5411
- VIN:
- 5TDKDRBH8TS609388
New arrival
2026 Toyota Highlander
XSE AWD
6,034 mi
Wallingford, CT
16 mi away
Good Deal
$49,424
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 40,262
- Stock #:
- 627544A
- VIN:
- 5TDGZRBH3NS224976
Photos coming soon
New arrival
2022 Toyota Highlander
XLE AWD
40,262 mi
Wappingers Falls, NY
41 mi away
Good Deal
$32,990
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- Automatic
- Mileage:
- 73,534
- Stock #:
- 9392A
- VIN:
- 5TDJZRFH6JS557117
Price drop
-$1,900
2018 Toyota Highlander
XLE AWD
73,534 mi
Cortlandt Manor, NY
45 mi away
No Rating
$25,888
$23,988
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 95,015
- Stock #:
- 9382A
- VIN:
- 5TDJZRFH0KS602392
2019 Toyota Highlander
XLE AWD
95,015 mi
Cortlandt Manor, NY
45 mi away
No Rating
$23,988
- 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:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 100,152
- Stock #:
- 9389A
- VIN:
- 5TDGZRBH0MS088644
2021 Toyota Highlander
XLE AWD
100,152 mi
Cortlandt Manor, NY
45 mi away
No Rating
$26,788
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 79,496
- Stock #:
- 9398A
- VIN:
- 5TDCZRBH8LS028897
2020 Toyota Highlander
L AWD
79,496 mi
Cortlandt Manor, NY
45 mi away
No Rating
$26,988
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 113,829
- Stock #:
- 26532A
- VIN:
- 5TDDZRFH5KS729474
2019 Toyota Highlander
Limited Platinum AWD
113,829 mi
Westbrook, CT
39 mi away
Overpriced
$26,870
- 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:
- 47,725
- Stock #:
- N7077A
- VIN:
- 5TDJZRBH0MS076595
Sponsored Listing
2021 Toyota Highlander
XSE AWD
47,725 mi
Cheshire, CT
12 mi away
Good Deal
$33,473
- 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:
- Cockpit Red
- Transmission:
- Automatic
- Mileage:
- 49,282
- Stock #:
- U33414
- VIN:
- 5TDKDRBH1PS526214
Sponsored by Riverhead Toyota
2023 Toyota Highlander
XSE AWD
49,282 mi
Riverhead, NY
47 mi away
Fair Deal
$37,920
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,893
- Stock #:
- UP43719
- VIN:
- 5TDKDRBH0SS579284
New arrival
Sponsored Listing
2025 Toyota Highlander
XLE AWD
24,893 mi
Hartford, CT
30 mi away
Fair Deal
$44,594
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,034
- Stock #:
- P5411
- VIN:
- 5TDKDRBH8TS609388
New arrival
Sponsored Listing
2026 Toyota Highlander
XSE AWD
6,034 mi
Wallingford, CT
16 mi away
Good Deal
$49,424
- 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:
- 47,725
- Stock #:
- N7077A
- VIN:
- 5TDJZRBH0MS076595
2021 Toyota Highlander
XSE AWD
47,725 mi
Cheshire, CT
12 mi away
Good Deal
$33,473
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 86,715
- Stock #:
- 627362A
- VIN:
- 5TDLZRBH0NS244486
2022 Toyota Highlander
XSE AWD
86,715 mi
Wappingers Falls, NY
41 mi away
Good Deal
$30,692
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,893
- Stock #:
- UP43719
- VIN:
- 5TDKDRBH0SS579284
New arrival
2025 Toyota Highlander
XLE AWD
24,893 mi
Hartford, CT
30 mi away
Fair Deal
$44,594
- 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:
- Cockpit Red
- Transmission:
- Automatic
- Mileage:
- 49,282
- Stock #:
- U33414
- VIN:
- 5TDKDRBH1PS526214
2023 Toyota Highlander
XSE AWD
49,282 mi
Riverhead, NY
47 mi away
Fair Deal
$37,920
- 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:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,242
- Stock #:
- 625313A
- VIN:
- 5TDJZRFH2KS600353
2019 Toyota Highlander
SE AWD
97,242 mi
Wappingers Falls, NY
41 mi away
Good Deal
$23,991
- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 6,034
- Stock #:
- P5411
- VIN:
- 5TDKDRBH8TS609388
New arrival
2026 Toyota Highlander
XSE AWD
6,034 mi
Wallingford, CT
16 mi away
Good Deal
$49,424
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 40,262
- Stock #:
- 627544A
- VIN:
- 5TDGZRBH3NS224976
Photos coming soon
New arrival
2022 Toyota Highlander
XLE AWD
40,262 mi
Wappingers Falls, NY
41 mi away
Good Deal
$32,990
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- Automatic
- Mileage:
- 73,534
- Stock #:
- 9392A
- VIN:
- 5TDJZRFH6JS557117
Price drop
-$1,900
2018 Toyota Highlander
XLE AWD
73,534 mi
Cortlandt Manor, NY
45 mi away
No Rating
$25,888
$23,988
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 95,015
- Stock #:
- 9382A
- VIN:
- 5TDJZRFH0KS602392
2019 Toyota Highlander
XLE AWD
95,015 mi
Cortlandt Manor, NY
45 mi away
No Rating
$23,988
- 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:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 100,152
- Stock #:
- 9389A
- VIN:
- 5TDGZRBH0MS088644
2021 Toyota Highlander
XLE AWD
100,152 mi
Cortlandt Manor, NY
45 mi away
No Rating
$26,788
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 79,496
- Stock #:
- 9398A
- VIN:
- 5TDCZRBH8LS028897
2020 Toyota Highlander
L AWD
79,496 mi
Cortlandt Manor, NY
45 mi away
No Rating
$26,988
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 113,829
- Stock #:
- 26532A
- VIN:
- 5TDDZRFH5KS729474
2019 Toyota Highlander
Limited Platinum AWD
113,829 mi
Westbrook, CT
39 mi away
Overpriced
$26,870
- 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:
- 47,725
- Stock #:
- N7077A
- VIN:
- 5TDJZRBH0MS076595
Sponsored Listing
2021 Toyota Highlander
XSE AWD
47,725 mi
Cheshire, CT
12 mi away
Good Deal
$33,473
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