Used Toyota Highlander for Sale in Windsor, CT
Shop for a versatile Toyota Highlander in the city where Adaora was born
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1,068 listings
- New Listing$11,995great price$2,891 below market
- 124,945 miles
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
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Located in Naugatuck, CT / 30 miles away from Windsor, CT
- Experience the power and efficiency of a robust 3.5L V6 engine with 270 horsepower. - Enjoy luxurious comfort with premium leather interiors and ad...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EHXCS134611
Stock: 134611N
Certified Pre-Owned: No - $13,495great price$2,801 below market
- 99,437 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
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Located in Naugatuck, CT / 30 miles away from Windsor, CT
- Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270hp. - Luxurious leather interior ensures comfort an...
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH0CS160389
Stock: 160389N
Certified Pre-Owned: No - New Listing$37,745great price$3,552 below market
- 24,575 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Lia Toyota of Northampton (32 mi away)
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Located in Northampton, MA / 32 miles away from Windsor, CT
Recent Arrival! One Owner - Clean Car Fax, AWD. 21/28 City/Highway MPGToyota Gold Certified Details:* Roadside Assistance for 7 Year / 100,000 Mile. S...
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: 5TDKDRBH4RS562014
Stock: RS562014R
Certified Pre-Owned: Yes
Listed since: 08-27-2025 - $14,995great price$1,991 below market
- 131,332 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
Close
Located in Naugatuck, CT / 30 miles away from Windsor, CT
- **Proven Reliability**: Award-winning 2016 Toyota Highlander XLE with a 3.5L V6 engine, recognized by Edmunds, J.D. Power, and Kelley Blue Book for ...
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFH0GS240351
Stock: 240351N
Certified Pre-Owned: No - $21,495great price$2,156 below market
- 97,051 miles
- No accidents, 4 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
Close
Located in Naugatuck, CT / 30 miles away from Windsor, CT
- **Low Mileage & Powerful Performance**: With only 97,051 miles, this 2018 Toyota Highlander SE is equipped with a robust 3.5L V6 engine delivering 2...
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: 5TDJZRFH1JS822414
Stock: 822414N
Certified Pre-Owned: No - Price Drop$22,976great price$1,934 below market
- 101,226 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Balise Subaru of Hadley (34 mi away)
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Located in Hadley, MA / 34 miles away from Windsor, CT
2019 Toyota Highlander in bold Midnight Black Metallic, powered by a strong 3.5L V6 engine paired with an 8-speed automatic transmission with ECT-i. T...
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: 5TDJZRFH6KS567115
Stock: S25015A
Certified Pre-Owned: No
Listed since: 07-12-2025 - $6,450good price$1,954 below market
- 144,525 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 16 City / 22 Hwy MPG
- Choice Motor Car (18 mi away)
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Located in Plainville, CT / 18 miles away from Windsor, CT
Nice, clean, loaded up Highlander in great condition inside and out. Leather seats, power sliding sunroof, 4wd, power windows locks and seat, nice ne...
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:
19 Combined MPG (16 City/22 Highway)
Listing Information:
VIN: JTEEP21A550080550
Stock: 080550
Certified Pre-Owned: No
Listed since: 09-10-2024 - New Listing$23,998great price$2,191 below market
- 107,897 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Hartford (5 mi away)
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Located in Hartford, CT / 5 miles away from Windsor, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3LS017517
Stock: 27545282
Certified Pre-Owned: No - Price Drop$28,900great price$1,514 below market
- 99,943 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Charles Toyota (39 mi away)
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Located in Norwich, CT / 39 miles away from Windsor, CT
2021 Toyota Highlander XSE 4D Sport Utility AWD in Blueprint!!! ONE Owner!!! Heated Leather Front Bucket Seats, Power driver seat, Navigation System, ...
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: 5TDJZRBH9MS061268
Stock: 56448
Certified Pre-Owned: No
Listed since: 08-12-2025 - $11,995good price$1,698 below market
- 118,333 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
Close
Located in Naugatuck, CT / 30 miles away from Windsor, CT
- **Proven Reliability:** Award-winning dependability and quality from J.D. Power and Kelley Blue Book. - **Powerful Performance:** Robust 3.5L V6 en...
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH1CS101004
Stock: 101004N
Certified Pre-Owned: No - $18,990good price$1,547 below market
- 126,409 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Toyota of Colchester (26 mi away)
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Located in Colchester, CT / 26 miles away from Windsor, CT
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: 5TDJZRFH9JS863793
Stock: 20256A
Certified Pre-Owned: No
Listed since: 07-19-2025 - $23,998good price$1,273 below market
- 92,986 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Ocean Honda Groton (46 mi away)
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Located in Groton, CT / 46 miles away from Windsor, CT
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, He...
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: 5TDJZRFH6KS626583
Stock: 6E07044
Certified Pre-Owned: No
Listed since: 07-17-2025 - $33,211fair price$691 below market
- 62,986 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Lia Toyota of Wilbraham (22 mi away)
Close
Located in Wilbraham, MA / 22 miles away from Windsor, CT
Blueprint 2022 Toyota Highlander XLE 3.5L V6 DOHC 8-Speed Automatic AWDClean Car-Fax *, Service Records Available *, Back Up Camera *, Bluetooth Smart...
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: 5TDGZRBH3NS596205
Stock: NS596205T
Certified Pre-Owned: No
Listed since: 07-15-2025 - $10,995good price$1,364 below market
- 113,382 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (30 mi away)
Close
Located in Naugatuck, CT / 30 miles away from Windsor, CT
- Reliable and powerful 3.5L V6 engine with 270 horsepower - Spacious interior with second-row rear vents and privacy glass - Award-winning family v...
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH8BS062068
Stock: 62068N
Certified Pre-Owned: No - Price Drop$39,798good price$1,340 below market
- 31,859 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- McGee Toyota of Putnam (41 mi away)
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Located in Putnam, CT / 41 miles away from Windsor, CT
McGee Toyota of Putnam is proud to present you with this 2024 Toyota Highlander XLE! ---------- ONE (1) OWNER TRADE-IN, CLEAN CARFAX, AWD, 2.4L 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/28 Highway)
Listing Information:
VIN: 5TDKDRBH4RS529403
Stock: 25792TA
Certified Pre-Owned: No
Listed since: 07-17-2025 - $24,206fair price$263 below market
- 88,640 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Lia Toyota of Wilbraham (22 mi away)
Close
Located in Wilbraham, MA / 22 miles away from Windsor, CT
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: 5TDJZRFH5JS559067
Stock: JS559067T
Certified Pre-Owned: No
Listed since: 06-30-2025 - $40,995fair price$430 below market
- 18,718 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Greentree Toyota (50 mi away)
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Located in Danbury, CT / 50 miles away from Windsor, CT
Recent Arrival!Certified. CARFAX One-Owner. 2022 Toyota Highlander XSE AWDAWD, All Weather Floor & Cargo Liner (TMS), Apple CarPlay/Android Auto, Bl...
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: 5TDLZRBH7NS240998
Stock: U22721
Certified Pre-Owned: Yes
Listed since: 08-20-2025 - New Listing$27,976good price$1,157 below market
- 70,465 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Balise Subaru of Hadley (34 mi away)
Close
Located in Hadley, MA / 34 miles away from Windsor, CT
This 2019 Toyota Highlander Limited in Midnight Black Metallic offers a perfect blend of power, comfort, and advanced safety features. Equipped with 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH2KS729688
Stock: S25172A
Certified Pre-Owned: No
Listed since: 08-27-2025 - $39,990fair price$100 above market
- 18,773 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Sarat Ford Lincoln (16 mi away)
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Located in Agawam, MA / 16 miles away from Windsor, CT
Looking for a clean, well-cared for 2023 Toyota Highlander? This is it. This Toyota Highlander XLE has a tough exterior complemented by a well-designe...
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: 5TDKDRBH4PS524120
Stock: E0703A
Certified Pre-Owned: No
Listed since: 08-14-2025 - New Listing$36,998good price$1,901 below market
- 28,568 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Herb Chambers Toyota of Auburn (47 mi away)
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Located in Auburn, MA / 47 miles away from Windsor, CT
INSPECTION COMPLETED Every Herb Chambers pre-owned vehicle receives a complete multi-point inspection by factory trained technicians who inspect the t...
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: 5TDKDRBH0PS045371
Stock: A286215A
Certified Pre-Owned: No
Listed since: 08-27-2025 - Price Drop$29,298good price$900 below market
- 71,824 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- McGee Toyota of Putnam (41 mi away)
Close
Located in Putnam, CT / 41 miles away from Windsor, CT
Recent Arrival!AWD.Here at McGee Toyota of Dudley, we take pride in being a family owned business, with over 40 years of automotive experience in ...
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: 5TDHZRBH8LS037086
Stock: 25904A
Certified Pre-Owned: No
Listed since: 08-21-2025
Showing 1 - 21 out of 1,068 listings
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