CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Toyota Highlander for Sale near Chesapeake, VA

539 results
Chesapeake, VA
2017 Toyota Highlander LE Plus AWD Winners Circle Chrysler Dodge Jeep Ram

2017 Toyota Highlander

LE Plus AWD

118,144 miles

$19,039

Fair Deal
Franklin, VA
42 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:
Midnight Black Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
118,144
Stock number:
FP3383
VIN:
5TDBZRFH2HS377471

Sponsored

2005 Toyota Highlander Base

2005 Toyota Highlander

Base

180,250 miles

$5,757

Fair Deal
Virginia Beach, VA
7 mi away
Year:
2005
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
160 hp 2.4L I4
Exterior color:
Green
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
Automatic
Mileage:
180,250
Stock number:
048153MT
VIN:
JTEGP21AX50048153

Sponsored

2016 Toyota Highlander XLE

2016 Toyota Highlander

XLE

144,897 miles

$16,995

Fair Deal
Virginia Beach, VA
9 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:
Green
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Tan)
Transmission:
6-Speed Automatic
Mileage:
144,897
VIN:
5TDKKRFH9GS152967

Sponsored

2016 Toyota Highlander

2016 Toyota Highlander

Limited

68,941 miles

$21,927

Great Deal
Norfolk, VA
8 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:
Predawn Gray Mica
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
6-Speed Automatic Overdrive
Mileage:
68,941
Stock number:
F260124136T1B
VIN:
5TDYKRFH7GS121825

2013 Toyota Highlander Plus AWD

2013 Toyota Highlander

Plus AWD

181,064 miles

$8,995

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:
Blue
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
5-Speed Automatic
Mileage:
181,064
Stock number:
0035
VIN:
5TDBK3EH1DS196228

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

L FWD

58,205 miles

$27,000

Good Deal
Newport News, VA
32 mi away
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:
Midnight Black Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
58,205
Stock number:
UX10031
VIN:
5TDKDRAH3PS504393

Preparing for a close up...

Photos coming soon

2021 Toyota Highlander

L FWD

92,589 miles

$21,995

Good Deal
Gloucester, VA
47 mi away
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:
8-Speed Automatic
Mileage:
92,589
Stock number:
137251
VIN:
5TDCZRAH2MS065995

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE AWD

44,013 miles

$33,669

Good Deal
Newport News, VA
32 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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
44,013
Stock number:
U260214447T1
VIN:
5TDHZRBH3NS252460

Preparing for a close up...

Photos coming soon

2019 Toyota Highlander

LE FWD

45,524 miles

$25,447

Fair Deal
Store transfer to Virginia Beach, VA
859 mi away • Price includes $449 shipping Price includes $449 shipping
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:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
45,524
Stock number:
27982592
VIN:
5TDZZRFH7KS369517

Preparing for a close up...

Photos coming soon

2018 Toyota Highlander

XLE AWD

95,344 miles

$22,500

Good 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:
Black
Transmission:
8-Speed Automatic
Mileage:
95,344
Stock number:
35172J
VIN:
5TDJZRFH6JS911167

Preparing for a close up...

Photos coming soon

2008 Toyota Highlander

Sport 4WD

194,970 miles

$5,995

Good Deal
Virginia Beach, VA
6 mi away
Year:
2008
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Classic Silver Metallic
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
5-Speed Automatic
Mileage:
194,970
VIN:
JTEES43A182096177

Sponsored

  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 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 Chesapeake, VA?

The average Toyota Highlander costs about $27,715.38. The average price has decreased by -3.5% since last year. The 539 for sale near Chesapeake, VA on CarGurus, range from $3,995 to $56,998 in price.

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

539 out of 539 for sale near Chesapeake, VA have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

  • 2027 Toyota Highlander in Chesapeake VA

  • 2026 Toyota Highlander in Chesapeake VA

  • 2025 Toyota Highlander in Chesapeake VA

  • 2024 Toyota Highlander

  • 2023 Toyota Highlander

  • 2022 Toyota Highlander

  • Used Toyota Highlander for Sale Under $10,000 Near Chesapeake

  • Used Toyota Highlander for Sale Under $15,000 Near Chesapeake

  • Used Toyota Highlander for Sale Under $20,000 Near Chesapeake

  • Used Toyota Highlander for Sale Under $25,000 Near Chesapeake

  • Used Toyota Highlander for Sale Under $30,000 Near Chesapeake

  • Used Toyota Highlander for Sale Under $40,000 Near Chesapeake

  • Used White Toyota Highlander for Sale in Chesapeake

  • Used Blue Toyota Highlander for Sale in Chesapeake

  • Used Red Toyota Highlander for Sale in Chesapeake

  • Used Black Toyota Highlander for Sale in Chesapeake

  • Used Silver Toyota Highlander for Sale in Chesapeake

  • Used Gray Toyota Highlander for Sale in Chesapeake

  • Toyota Highlander XLE AWD

  • Toyota Highlander Limited AWD

  • Toyota Highlander LE AWD

  • Toyota Highlander XLE FWD

  • Toyota Highlander LE FWD

  • Toyota Highlander XSE AWD

  • Toyota Highlander Platinum AWD

  • Toyota Highlander XLE

  • Toyota Highlander L FWD

  • Toyota Highlander Limited FWD

  • Toyota Sedans for Sale in Chesapeake VA

  • Toyota SUVs & Crossovers for Sale in Chesapeake VA

  • Old Toyota Pickups for Sale in Chesapeake VA

  • Used Toyota Electric Cars for Sale

  • Reliable Cars For Sale in Chesapeake VA

  • Toyota Trucks for Sale in Chesapeake VA

  • Best 3-Row SUVs For Sale in Chesapeake VA

  • Used Toyota Highlander for Sale with Low Mileage in Chesapeake

  • Used SUVs / Crossovers for Sale with Low Mileage in Chesapeake

  • New Toyota Highlander in Chesapeake VA

  • Certified Used Toyota Highlander in Chesapeake VA

  • Cadillac SRX in Chesapeake VA

  • Ford Escape in Chesapeake VA

  • Hyundai Veracruz in Chesapeake VA

  • Toyota Highlander in Norfolk VA

  • Toyota Highlander in Elizabeth City NC

  • Toyota Highlander in Williamsburg VA

  • Toyota Highlander in Richmond VA

  • Toyota Highlander in Greenville NC

  • Toyota Highlander in Rocky Mount NC

  • Toyota Highlander in New Bern NC

  • Toyota Highlander in Salisbury MD

  • Toyota Highlander in Fredericksburg VA

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage in Chesapeake

  • Used SUVs / Crossovers for Sale with Low Mileage in Chesapeake

  • Used Hatchbacks for Sale with Low Mileage in Chesapeake

  • Used Convertibles for Sale with Low Mileage in Chesapeake

  • Used Vans for Sale with Low Mileage in Chesapeake

  • Used Minivans for Sale with Low Mileage in Chesapeake

  • Used Pickup Trucks for Sale with Low Mileage in Chesapeake

  • Used Coupes for Sale with Low Mileage in Chesapeake

  • Used Wagons for Sale with Low Mileage in Chesapeake

  • Hall Toyota of Elizabeth City

  • Classic Toyota of Hampton

  • Checkered Flag Toyota

  • Hall Toyota Virginia Beach

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.