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Used Toyota Highlander for Sale near Chesapeake, VA

684 results
Chesapeake, VA
2017 Toyota Highlander XLE AWD Paragon Automotive

2017 Toyota Highlander

XLE AWD

93,853 miles

$22,955

Fair Deal
Virginia Beach, VA
4 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:
White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
8-Speed Automatic
Mileage:
93,853
Stock number:
1785
VIN:
5TDJZRFH6HS479156

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2012 Toyota Highlander Limited AWD

2012 Toyota Highlander

Limited AWD

103,431 miles

$15,255

Good Deal
Virginia Beach, VA
4 mi away
Year:
2012
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
103,431
Stock number:
1807
VIN:
5TDDK3EH1CS170459

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2023 Toyota Highlander XLE AWD

2023 Toyota Highlander

XLE AWD

38,860 miles

$37,000

Fair Deal
Virginia Beach, VA
6 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:
38,860
Stock number:
10251109A
VIN:
5TDKDRBHXPS528284

Sponsored

2018 Toyota Highlander LE Plus AWD

2018 Toyota Highlander

LE Plus AWD

56,377 miles

$24,000

Fair Deal
Chesapeake, VA
3 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 (Blizzard Pearl)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
56,377
Stock number:
35013AFC
VIN:
5TDBZRFH7JS884260

2013 Toyota Highlander Limited AWD

2013 Toyota Highlander

Limited AWD

140,091 miles

$12,135

Great Deal
Portsmouth, VA
10 mi away
Year:
2013
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Nautical Blue Metallic
Fuel type:
Gasoline
Interior color:
Brown (Sand Beige)
Transmission:
5-Speed Automatic Overdrive
Mileage:
140,091
Stock number:
178670
VIN:
5TDDK3EH2DS178670

2019 Toyota Highlander LE FWD

2019 Toyota Highlander

LE FWD

63,884 miles

$21,995

Fair Deal
Elizabeth City, NC
29 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
63,884
Stock number:
KS056897B
VIN:
5TDZARFH2KS056897

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2016 Toyota Highlander

Limited AWD

107,739 miles

$20,000

Good Deal
Chesapeake, VA
3 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver Sky Metallic
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
107,739
Stock number:
34933NG
VIN:
5TDDKRFH9GS330420

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2018 Toyota Highlander

Limited AWD

120,349 miles

$20,949

Great Deal
Virginia Beach, VA
6 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:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
120,349
Stock number:
TWZ46037
VIN:
5TDDZRFH3JS832407

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2024 Toyota Highlander

Limited AWD

29,756 miles

$41,000

Great Deal
Virginia Beach, VA
8 mi away
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:
Moon Dust
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
29,756
Stock number:
426107A
VIN:
5TDKDRBH0RS567890

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2012 Toyota Highlander

Limited AWD

103,667 miles

$14,990

Fair Deal
Williamsburg, VA
47 mi away
Year:
2012
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Blue
Fuel type:
Gasoline
Transmission:
5-Speed Automatic Overdrive
Mileage:
103,667
Stock number:
5K588A
VIN:
5TDDK3EH3CS147443

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2022 Toyota Highlander

Platinum AWD

30,717 miles

$41,690

Good Deal
Virginia Beach, VA
7 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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,717
Stock number:
T73737A
VIN:
5TDFZRBH8NS180257

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2013 Toyota Highlander

Limited AWD

128,718 miles

$13,990

Good Deal
Williamsburg, VA
47 mi away
Year:
2013
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic Overdrive
Mileage:
128,718
Stock number:
5K595A
VIN:
5TDDK3EH8DS178270

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2017 Toyota Highlander

XLE AWD

114,761 miles

$19,200

Great Deal
Virginia Beach, VA
6 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:
Predawn Gray Mica
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
6-Speed Automatic
Mileage:
114,761
Stock number:
8902
VIN:
5TDJZRFH2HS466310

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2023 Toyota Highlander

XLE AWD

21,249 miles

$38,097

Good Deal
Store transfer to Virginia Beach, VA
286 mi away • Price includes $99 shipping Price includes $99 shipping
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:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
21,249
Stock number:
28163694
VIN:
5TDKDRBH9PS046793

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2022 Toyota Highlander

XLE AWD

57,431 miles

$31,999

Good Deal
Norfolk, VA
11 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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Mileage:
57,431
Stock number:
P2018
VIN:
5TDGZRBH4NS590185

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2021 Toyota Highlander

Limited FWD

40,156 miles

$34,997

Fair Deal
Store transfer to Virginia Beach, VA
2,473 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,156
Stock number:
27682783
VIN:
5TDYZRAHXMS070688

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2016 Toyota Highlander

Limited Platinum

80,188 miles

$23,250

Fair Deal
Virginia Beach, VA
6 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
80,188
Stock number:
14400
VIN:
5TDYKRFH8GS146118

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / Virginia
  5. / Chesapeake
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander

Summary

  • With 6,394 currently listed for sale on CarGurus and an average price of $33,778.00, 36.1% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2022 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it an 8.2 / 10.
  • 84.2% of 2022 Highlander models on CarGurus are accident free.
  • The 2022 Toyota Highlander hybrid achieved an impressive 35 mpg combined, making it one of the most fuel-efficient midsize SUVs available.

Why it stands out

The 2022 Toyota Highlander excels as a versatile family hauler, offering spacious three-row seating and ample cargo capacity, making it ideal for transporting kids and their gear. Its robust V6 engine ensures reliable performance, while standard safety features and high safety ratings provide peace of mind for families on the go. Additionally, the Highlander's blend of practicality and comfort, along with various trim options to suit different budgets, solidifies its position as a top choice in the midsize SUV segment.

Other model years to consider

When considering the Toyota Highlander, the 2015 and 2019 model years stand out as particularly suitable alternatives due to their affordability and strong quality ratings. The 2015 Highlander offers a great balance of value at an average price of around $16,812, while still maintaining a high user rating of 4.8/5 and a favorable inventory of good deals. Similarly, the 2019 model provides a modern option with an average price of approximately $24,070 and a solid user rating of 4.6/5, making it an attractive choice for those seeking reliability without stretching their budget.

Additionally, for buyers prioritizing budget-friendly options, the 2012 Highlander presents a compelling case with its low average price of about $11,483 and excellent user rating of 4.7/5. Overall, these model years offer quality vehicles with good market availability that cater to various needs and budgets.

Model years to approach with caution

When considering the Toyota Highlander, specific model years warrant a cautious approach due to their market positioning and user feedback. For instance, the 2014 and 2018 models show relatively low percentages of good or great deals at 67% and 64%, respectively, suggesting that many buyers may not feel they are receiving fair value for their investment. Additionally, despite decent user ratings, the consistent trend of high percentages of unsatisfactory deals indicates potential concerns regarding long-term value retention and overall satisfaction among owners.

These recommendations are based on CarGurus' proprietary market data from December 9, 2025, 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.

Kristy E
5.0
Reviewed a 2010 Toyota Highlander on Jan 25, 2024

Great car that has a reputation for durability. Love the features.

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

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Chesapeake, VA?

The average Toyota Highlander costs about $27,555.80. The average price has decreased by -5.9% since last year. The 684 for sale near Chesapeake, VA on CarGurus, range from $4,131 to $54,998 in price.

How many Toyota Highlander vehicles in Chesapeake, VA have no reported accidents or damage?

684 out of 684 for sale near Chesapeake, VA have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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