Skip to FiltersReport abuse
2,343 listings
- $30,990fair price$260 below market
- 56,690 miles
- 2 accidents, 2 owners, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Riverhead Hyundai (31 mi away)
Close
Located in Riverhead, NY / 31 miles away from Bridgeport, CT
Gy 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD.Head East to pay the least! 20/27 City/Highway MPGAwards:* ALG Residual Value Awa...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH8MS137766
Stock: U21734
Certified Pre-Owned: No
Listed since: 03-27-2025 - $32,499fair price$164 below market
- 41,308 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Albuquerque, NM / 1,852 miles away from Bridgeport, CT
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: 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: 5TDKDRAH9PS016565
Stock: 7W5C2J
Certified Pre-Owned: No
Listed since: 03-28-2025 - Price Drop$34,719fair price$590 above market
- 33,159 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- McGee Toyota of Putnam (86 mi away)
Close
Located in Putnam, CT / 86 miles away from Bridgeport, CT
McGee Toyota of Putnam is proud to present you with this 2021 Toyota Highlander XLE AWD! ---------- CLEAN CARFAX, AWD, 3.5L V6 ENGINE, 8-SPEED AUT...
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: 5TDGZRBH5MS098666
Stock: P3262
Certified Pre-Owned: No
Listed since: 04-07-2025 - 36,122 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,632 miles away from Bridgeport, CT
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: 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: 5TDKDRBH2PS032850
Stock: 2003740953
Certified Pre-Owned: No
Listed since: 05-19-2025- $37,777fair price$452 below market
- 41,849 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- City World Ford (40 mi away)
Close
Located in Bronx, NY / 40 miles away from Bridgeport, CT
NO DEALER FEE'S!!! Visit us at WWW.CITYWORLDFORD.NET OR call 7**-8**-7*** to check out one of the largest and most thoroughly serviced pre-owned lots ...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH6PS038781
Stock: F13554
Certified Pre-Owned: No
Listed since: 05-10-2025 - Price Drop
- 44,707 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Salt Lake City, UT / 1,999 miles away from Bridgeport, CT
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: 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: 5TDKDRBH4PS039332
Stock: 2003747772
Certified Pre-Owned: No
Listed since: 05-20-2025 - New Listing$28,990fair price$132 below market
- 93,665 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Philadelphia, PA / 127 miles away from Bridgeport, CT
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: 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: 5TDKDRAH9PS016632
Stock: 2003773220
Certified Pre-Owned: No
Listed since: 06-05-2025 - $33,998fair price$673 above market
- 47,538 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to CT*
Close
Located in Irvine, CA / 2,471 miles away from Bridgeport, CT
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: No
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS007972
Stock: 27453046
Certified Pre-Owned: No - Price Drop$41,998fair price$1,173 above market
- 40,464 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to CT*
Close
Located in Costa Mesa, CA / 2,479 miles away from Bridgeport, CT
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: No
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS507581
Stock: 27329224
Certified Pre-Owned: No - New Listing$29,682fair price
- 77,416 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,412 miles away from Bridgeport, CT
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite Radio,Tur...
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: 5TDKDRAH2PS504904
Stock: PS504904P
Certified Pre-Owned: No - $43,278fair price$607 below market
- 39,293 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Cranberry, PA / 359 miles away from Bridgeport, CT
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free L...
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: 5TDKDRBH0PS003203
Stock: T003203P
Certified Pre-Owned: No - $39,999fair price$650 above market
- 38,150 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Metairie, LA / 1,223 miles away from Bridgeport, CT
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH8PS508728
Stock: 8DDX77
Certified Pre-Owned: No
Listed since: 05-19-2025 - $38,490fair price$440 above market
- 55,305 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Chesapeake, VA / 345 miles away from Bridgeport, CT
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 - New Listing$39,998fair price
- 14,003 miles
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to CT*
Close
Located in Plano, TX / 1,411 miles away from Bridgeport, CT
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS519596
Stock: 25853739
Certified Pre-Owned: No - Price Drop$36,982fair price$329 below market
- 50,550 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Pocatello, ID / 1,997 miles away from Bridgeport, CT
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats...
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: 5TDKDRBH0PS500574
Stock: PS500574T
Certified Pre-Owned: No - 72,196 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Honda of Westport (7 mi away)
- Home delivery*
Close
Located in Westport, CT / 7 miles away from Bridgeport, CT
CARFAX One-Owner.Black 2021 Toyota Highlander LE 4D Sport Utility AWD 8-Speed Automatic 3.5L V6 DOHC 20/27 City/Highway MPG
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: 5TDBZRBH7MS072063
Stock: 30983
Certified Pre-Owned: No
Listed since: 04-29-2025- New Listing$44,998fair price$851 above market
- 16,708 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to CT*
Close
Located in Raleigh, NC / 466 miles away from Bridgeport, CT
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS016822
Stock: 27249604
Certified Pre-Owned: No - $40,998fair price$589 below market
- 18,533 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MD to CT*
Close
Located in White Marsh, MD / 212 miles away from Bridgeport, CT
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS042840
Stock: 27450482
Certified Pre-Owned: No - 36,969 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Highlands Ranch, CO / 1,664 miles away from Bridgeport, CT
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH0PS046651
Stock: 7WS540
Certified Pre-Owned: No
Listed since: 04-28-2025- Price Drop$40,995fair price$674 above market
- 40,353 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Lexus of Englewood (45 mi away)
Close
Located in Englewood, NJ / 45 miles away from Bridgeport, CT
Recent Arrival! 2023 Toyota Highlander XSE AWD Wind Chill Pearl 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed AutomaticAWD, Heated fron...
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: 5TDKDRBH1PS004280
Stock: 515643A
Certified Pre-Owned: No
Listed since: 05-29-2025 - Price Drop$39,989fair price$575 above market
- 26,487 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Speedcraft Acura (95 mi away)
Close
Located in West Warwick, RI / 95 miles away from Bridgeport, CT
Recent Arrival! Priced below KBB Fair Purchase Price! CARFAX One-Owner.Moonroof, Heated Seats, Bluetooth, Back Up Camera, Third Row Seating, Local Tra...
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: 5TDKDRBH3PS039077
Stock: A25362S-1
Certified Pre-Owned: No
Listed since: 05-25-2025
Showing 400 - 420 out of 2,343 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
Used 2021 Toyota Highlander in Bridgeport, CT 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 | $31,229 | $33,578 | $35,934 |
| Clean | $30,564 | $32,846 | $35,133 |
| Average | $29,456 | $31,627 | $33,797 |
| Rough | $28,016 | $30,041 | $32,062 |
The average list price of a used 2021 Toyota Highlander in Bridgeport, Connecticut is $36,998. The average mileage on a used Toyota Highlander 2021 for sale in Bridgeport, Connecticut is 43,879. Based on the average mileage of 43,879 for used 2021 Toyota Highlander for sale in Bridgeport, CT 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 Bridgeport, Connecticut to be $29,456.
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.