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2,160 listings
- $31,500fair price$467 below market
- 55,429 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
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Located in Richmond, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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: 5TDKDRAH8PS500114
Stock: J6879
Certified Pre-Owned: No
Listed since: 05-22-2025 - New Listing$25,504good price$1,086 below market
- 78,894 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Check out this great value! This vehicle glistens in the crowded fullsize SUV segment! All of the premium features expected of a Toyota are offered, i...
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: 5TDZZRAH1MS517588
Stock: 13170PP
Certified Pre-Owned: No
Listed since: 06-06-2025 - $39,998fair price$493 above market
- 26,293 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Sacramento, CA / 2,451 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: 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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH8MS537832
Stock: 27457296
Certified Pre-Owned: No - $38,490fair price$569 above market
- 55,305 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Hea...
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: 5TDKDRAH5PS500099
Stock: PS500099P
Certified Pre-Owned: No - $41,595fair price$248 below market
- 24,671 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Trust Auto (192 mi away)
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Located in Sykesville, MD / 192 miles away from Chesapeake, VA
Trust Auto is pleased to be currently offering this Loaded 2023 Toyota Highlander XSE AWD 7-Passanger SUV with 24,671mi. This Toyota includes: 50 STAT...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS001044
Stock: 001044
Certified Pre-Owned: No
Listed since: 05-09-2025 - $25,000fair price$278 below market
- 78,956 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Preston Ford of Denton (149 mi away)
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Located in Denton, MD / 149 miles away from Chesapeake, VA
AWD.Founded in 1975, Preston has been providing a friendly, no-hassle car buying experience for more than 45 years. We have been family owned and oper...
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: 5TDBZRFH2KS731612
Stock: H250116A
Certified Pre-Owned: No
Listed since: 03-24-2025 - Price Drop$32,998fair price$273 below market
- 46,097 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
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Located in Memphis, TN / 766 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: 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: 5TDGZRAH7MS087802
Stock: 27043574
Certified Pre-Owned: No - $22,995fair price$139 below market
- 115,504 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Master Auto Group (146 mi away)
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Located in Raleigh, NC / 146 miles away from Chesapeake, VA
All of our vehicles have been freshly serviced, inspected, and carry a clean tittle with a complimentary Carfax report. Bank and Credit Union financi...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH3KS322311
Stock: 322311
Certified Pre-Owned: No
Listed since: 10-25-2024 - $40,499fair price$40 below market
- 47,831 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Sir Walter Chevrolet (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
Recent Arrival! 2023 Toyota Highlander Limited Black ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/...
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: 5TDKDRAH8PS002821
Stock: PX6438
Certified Pre-Owned: No
Listed since: 06-03-2025 - New Listing$29,998good price$1,554 below market
- 80,462 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
Close
Located in Jackson, TN / 708 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: 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: 5TDLZRAH1MS084991
Stock: 27043189
Certified Pre-Owned: No - $32,707good price$1,385 below market
- 74,740 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Westgate Kia (140 mi away)
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Located in Wake Forest, NC / 140 miles away from Chesapeake, VA
Come see this vehicle and many more at Westgate Kia in Wake Forest!!, AWD, 20" Alloy Wheels, 3rd row seats: split-bench, Apple CarPlay/Android Auto, A...
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: 5TDDZRBH4MS076970
Stock: 42304XP
Certified Pre-Owned: No
Listed since: 12-13-2024 - Price Drop
- 48,269 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hampton Chevrolet (23 mi away)
- Home delivery*
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Located in Hampton, VA / 23 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Celestial Si 2023 Toyota Highlander XLEAt First Team Chevrolet Enjoy Your Ride with:- NO COST OIL CHANGES FOREVER!...
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: 5TDKDRAH9PS008403
Stock: PB11968
Certified Pre-Owned: No
Listed since: 04-17-2025 - Price Drop$29,980good price$1,198 below market
- 75,018 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Mark Jacobson Toyota (162 mi away)
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Located in Durham, NC / 162 miles away from Chesapeake, VA
Come to Mark Jacobson Toyota and check out this. 2021 Toyota Highlander XLE In our two story indoor showroom! Certified. Magnetic Gray Metallic AWD 8-...
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: 5TDGZRBH7MS543151
Stock: P16850
Certified Pre-Owned: No
Listed since: 04-23-2025 - New Listing$30,998fair price$730 above market
- 36,345 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AL to VA*
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Located in Hoover, AL / 643 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDZZRAH4MS036136
Stock: 27299983
Certified Pre-Owned: No - New Listing$34,697good price$1,021 below market
- 60,551 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
This vehicle won't be on the lot long! Packed with features and truly a pleasure to drive! It includes heated seats, telescoping steering wheel, a pow...
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: 5TDDZRBH4MS127335
Stock: 13167PP
Certified Pre-Owned: No
Listed since: 06-06-2025 - $35,986fair price$431 above market
- 60,488 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Thompson Buick GMC (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
This vehicle won't be on the lot long! It just arrived on our lot this past week! This model accommodates 7 passengers comfortably, and provides featu...
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: 5TDLZRBH0MS093261
Stock: 07353B
Certified Pre-Owned: No
Listed since: 04-04-2025 - $25,102fair price$549 below market
- 85,585 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Reynolds Subaru (147 mi away)
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Located in Orange, VA / 147 miles away from Chesapeake, VA
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH9KS588489
Stock: 38903P
Certified Pre-Owned: No
Listed since: 05-25-2025 - New Listing$33,998fair price
- 35,489 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Houston, TX / 1,200 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH5MS084378
Stock: 27353494
Certified Pre-Owned: No - Price Drop$36,592fair price$898 above market
- 43,741 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Haley Toyota of Richmond (90 mi away)
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Located in Midlothian, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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: 5TDKDRAH6PS009718
Stock: J6831
Certified Pre-Owned: No
Listed since: 05-13-2025 - $26,998fair price$322 below market
- 63,120 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Brandenton, FL / 741 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH3MS044847
Stock: 27312846
Certified Pre-Owned: No - Price Drop$33,900fair price$487 above market
- 38,259 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (149 mi away)
Close
Located in Suitland, MD / 149 miles away from Chesapeake, VA
2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, Toyota Safety Sens...
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: 5TDKDRBH7PS040300
Stock: B8803
Certified Pre-Owned: No
Listed since: 05-22-2025
Showing 316 - 336 out of 2,160 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 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $23,732 | $25,562 | $27,626 |
| Clean | $23,435 | $25,215 | $27,222 |
| Average | $22,940 | $24,636 | $26,548 |
| Rough | $22,295 | $23,884 | $25,673 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $32,644. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 58,621. Based on the average mileage of 58,621 for used 2023 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 2023 in Chesapeake, Virginia to be $22,940.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.