Skip to FiltersReport abuse
1,877 listings
- Not Priced
- 106,205 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Mr. Car of Glen Burnie (169 mi away)
Close
Located in Glen Burnie, MD / 169 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH8LS012491
Stock: CC012491B
Certified Pre-Owned: No
Listed since: 03-21-2025 - 61,860 miles
- Frame damage reported, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
Close
Located in Woodbridge, VA / 142 miles away from Chesapeake, VA
Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH5NS175690
Stock: 35474
Certified Pre-Owned: No- New Listing
- 60,023 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Frederick (173 mi away)
Close
Located in Gaithersburg, MD / 173 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH0LS522446
Stock: 26937233
Certified Pre-Owned: No - Price Drop$34,995great price$6,024 below market
- 46,732 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Platinum Auto Sales of Arlington Virginia (156 mi away)
Close
Located in Arlington, VA / 156 miles away from Chesapeake, VA
Non-smoker owner, Vehicle Runs Well, Smooth ride, All records in possession, Regularly maintained, Lots of storage, Arctic cold a/c, No pets, Seats as...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS507222
Stock: 507222
Certified Pre-Owned: No - $28,966great price$3,349 below market
- 33,836 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Global Auto Outlet (150 mi away)
Close
Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
Estimated monthly payment and estimated total purchase price include the Maryland processing fee of $800 (not required by law). Taxes and additional f...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH0PS504724
Stock: 504724
Certified Pre-Owned: No
Listed since: 11-16-2024 - $36,000great price$3,547 below market
- 40,758 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Toyota of Southern Maryland (108 mi away)
Close
Located in Lexington Park, MD / 108 miles away from Chesapeake, VA
ONE OWNER, AWD, SUNROOF, CLEAN CARFAX, LOCAL TRADE, SERVICED HERE, SIRRUS/XM RADIO, BACKUP CAMERA, ALLOY WHEELS, FOG LAMPS, Bluetooth , MARYLAND STAT...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBHXMS135345
Stock: U135345
Certified Pre-Owned: Yes
Listed since: 05-04-2025 - Price Drop$29,397great price$3,287 below market
- 37,671 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
Close
Located in Cary, NC / 155 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS041322
Stock: RPS041322
Certified Pre-Owned: No
Listed since: 04-01-2025 - Price Drop$22,797great price$2,289 below market
- 102,299 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Auto Park Honda (159 mi away)
Close
Located in Cary, NC / 159 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH5KS552013
Stock: CH109322B
Certified Pre-Owned: No
Listed since: 04-13-2025 - New ListingNot Priced
- Not provided
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
Close
Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2022 Toyota Highlander LE Recent Arrival!Magnetic Gray Metallic AWD. AWD 3.5L V6 DOHC 8-Speed Automatic 20/27 City/Highway MPG
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH3NS568737
Stock: 52A5520A
Certified Pre-Owned: No
Listed since: 05-31-2025 - $34,395great price$3,231 below market
- 46,150 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Capital Ford (144 mi away)
Close
Located in Raleigh, NC / 144 miles away from Chesapeake, VA
Leather, Sunroof, Heated Seats, Apple Carplay/Android Auto, Active Cruise Control, Heated Front Bucket Seats, Power Liftgate.Your Powerhouse Dealer!Ca...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS013639
Stock: PB60929
Certified Pre-Owned: No
Listed since: 01-20-2025 - $24,195great price
- 82,834 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,392 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH5MS088897
Stock: MS088897A
Certified Pre-Owned: No - Price Drop$26,923good price$2,419 below market
- 80,030 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 700 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH2MS516733
Stock: MS516733T
Certified Pre-Owned: No - $31,500great price$3,734 below market
- 71,995 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Kent County Motor Sales (169 mi away)
Close
Located in Dover, DE / 169 miles away from Chesapeake, VA
2021 Toyota Highlander Platinum 8-Speed Automatic 3.5L V6 DOHC Priced below KBB Fair Purchase Price! 20/27 City/Highway MPGAwards: * ALG Residual Valu...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH1MS075736
Stock: 40462A
Certified Pre-Owned: No
Listed since: 08-17-2024 - Price Drop$30,700great price$2,739 below market
- 44,779 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
Close
Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander LE 3rd row seats: split-bench, ABS brakes, Active Cruise Control, Alloy wheels, Brake assist, Electronic Stability Control, Fro...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS505218
Stock: R10799
Certified Pre-Owned: No
Listed since: 05-09-2025 - $32,981great price$2,981 below market
- 65,273 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Sheehy GMC of Fredericksburg (126 mi away)
Close
Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
2021 Toyota Highlander XSE AWD at Sheehy GMC Subaru of Fredericksburg! This Highlander has an exterior color of Magnetic Gray Metallic with Cockpit Re...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH4MS132361
Stock: T227266A
Certified Pre-Owned: No
Listed since: 04-15-2025 - New Listing$35,291great price$3,320 below market
- 50,262 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Sheehy Toyota of Laurel (169 mi away)
Close
Located in Laurel, MD / 169 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH3MS122014
Stock: A20807A
Certified Pre-Owned: Yes
Listed since: 05-10-2025 - $19,998great price$1,763 below market
- 141,865 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- CarHub (138 mi away)
Close
Located in Stafford, VA / 138 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFHXKS600505
Stock: 600505
Certified Pre-Owned: No - New Listing$24,922great price$1,867 below market
- 73,555 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 27 Hwy MPG
- Capital Chrysler Jeep Dodge Ram (148 mi away)
Close
Located in Garner, NC / 148 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH4KS569403
Stock: GAC11780
Certified Pre-Owned: No
Listed since: 04-03-2025 - $25,267great price$2,552 below market
- 75,085 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Lexus of Towson (186 mi away)
Close
Located in Towson, MD / 186 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH4KS579487
Stock: T2762AAA
Certified Pre-Owned: No
Listed since: 05-12-2025 - New Listing$33,998good price$2,545 below market
- 19,114 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax Virginia Beach (10 mi away)
Close
Located in Virginia Beach, VA / 10 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS513251
Stock: 27487087
Certified Pre-Owned: No - Price Drop$23,195good price$2,222 below market
- 128,387 miles
- 1 accident, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in North Brunswick, NJ / 273 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH1MS070221
Stock: SS044301A
Certified Pre-Owned: No
Showing 148 - 168 out of 1,877 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2020 Toyota Highlander in Chesapeake, VA Values
Estimated values
2020 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,266 | $29,607 | $31,861 |
| Clean | $26,561 | $28,831 | $31,016 |
| Average | $25,384 | $27,538 | $29,607 |
| Rough | $23,855 | $25,857 | $27,776 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $29,637. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 68,436. Based on the average mileage of 68,436 for used 2020 Toyota Highlander for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Toyota Highlander 2020 in Chesapeake, Virginia to be $25,384.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.