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2,204 listings
- Price Drop$33,900fair price$158 above market
- 47,320 miles
- No accidents, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Jim Coleman Toyota (166 mi away)
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Located in Bethesda, MD / 166 miles away from Chesapeake, VA
1 OWNER, CLEAN CARFAX, XLE-AWD, HEATED FRONT SEATS, LEATHER SEATS, NAVIGATION, POWER TILT/SLIDE MOONROOF, POWER LIFTGATE, BLIND SPOT, ANDROID AUTO/APP...
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: 5TDHZRBH7MS097734
Stock: 93740A
Certified Pre-Owned: No
Listed since: 05-01-2025 - New Listing$40,000fair price$833 above market
- 22,616 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander XLE CarFax 1 Owner, Local Trade, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS042951
Stock: 251846A
Certified Pre-Owned: No
Listed since: 06-06-2025 - Price Drop$33,998fair price$326 above market
- 48,435 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MA to VA*
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Located in North Attleboro, MA / 445 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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3MS531739
Stock: 27030643
Certified Pre-Owned: No - New Listing$29,997fair price$810 above market
- 59,171 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Lindsay Volkswagen of Manassas (156 mi away)
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Located in Manassas, VA / 156 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: 5TDJZRFH9KS728413
Stock: MVP11050
Certified Pre-Owned: No
Listed since: 06-05-2025 - New Listing$32,590fair price
- 62,494 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,195 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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: 5TDHZRAH4MS067673
Stock: 2003788609
Certified Pre-Owned: No
Listed since: 06-06-2025 - Price Drop$38,195fair price$336 above market
- 37,159 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in North Brunswick, NJ / 273 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheel...
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: 5TDDZRBH4MS559486
Stock: BTP11743
Certified Pre-Owned: No - Price Drop$29,999fair price$806 below market
- 65,100 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Tempe, AZ / 2,023 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH4MS038654
Stock: 8CGV2C
Certified Pre-Owned: No
Listed since: 03-04-2025 - Price Drop$35,005fair price$32 below market
- 56,100 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Helena, MT / 1,958 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote St...
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: 5TDLZRBH0MS056467
Stock: MS056467PC
Certified Pre-Owned: No - $33,950fair price$223 below market
- 39,745 miles
- 2 accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Easterns Automotive Group of Sterling / Direct Car Buying (170 mi away)
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Located in Sterling, VA / 170 miles away from Chesapeake, VA
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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: 5TDGZRBH2MS527410
Stock: 162331
Certified Pre-Owned: No
Listed since: 05-16-2025 - Price Drop$29,980fair price$262 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 - Price Drop$35,333fair price$506 below market
- 75,188 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Pocatello, ID / 1,952 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,K...
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: 5TDFZRBH2MS065216
Stock: MS065216A
Certified Pre-Owned: No - 79,746 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CMA's Honda of Lynchburg (172 mi away)
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Located in Lynchburg, VA / 172 miles away from Chesapeake, VA
Thank you for choosing CMA's Honda of Lynchburg, this Blizzard Pearl 2019 Toyota Highlander Limited is a great choice! Check out the following:No Acci...
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: 5TDYZRFH7KS328476
Stock: 16978A
Certified Pre-Owned: No
Listed since: 04-23-2025- Price Drop$38,998good price$1,348 below market
- 43,794 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
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Located in Reno, NV / 2,352 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: 5TDFZRBH4MS068148
Stock: 26745301
Certified Pre-Owned: No - $31,998fair price$1,247 below market
- 54,156 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AZ to VA*
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Located in Tolleson, AZ / 2,038 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDHZRAH1MS069591
Stock: 27450923
Certified Pre-Owned: No - 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: 04-16-2025 - Price Drop
- 41,888 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 578 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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: 5TDFZRBHXMS142169
Stock: 2003677629
Certified Pre-Owned: No
Listed since: 04-24-2025 - Price Drop$30,998fair price$214 below market
- 60,378 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax White Marsh (182 mi away)
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Located in White Marsh, MD / 182 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH8KS923240
Stock: 26925119
Certified Pre-Owned: No - New Listing$30,552fair price
- 85,064 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,189 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,Navigation System,R...
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: 5TDJZRAH1MS070290
Stock: MS070290A
Certified Pre-Owned: No - New Listing$33,998fair price$991 above market
- 50,349 miles
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
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Located in Buford, GA / 474 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH6MS521935
Stock: 26916097
Certified Pre-Owned: No - New Listing
- 43,510 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Nashville, TN / 588 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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: 5TDGZRBH6MS063618
Stock: 2003734210
Certified Pre-Owned: No
Listed since: 05-29-2025 - $32,286good price
- 61,477 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,189 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Heated Seats,Heated Steering Whe...
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: 5TDYZRAH5MS085082
Stock: MS085082P
Certified Pre-Owned: No
Showing 358 - 378 out of 2,204 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $28,936 | $31,006 | $33,081 |
| Clean | $28,320 | $30,331 | $32,344 |
| Average | $27,293 | $29,204 | $31,114 |
| Rough | $25,959 | $27,740 | $29,516 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $34,110. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 55,094. Based on the average mileage of 55,094 for used 2021 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 2021 in Chesapeake, Virginia to be $27,293.
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