CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Certified Toyota Highlander for Sale near Oakham, MA

38 results
Oakham, MA
2024 Toyota Highlander LE AWD Imperial Toyota

2024 Toyota Highlander

LE AWD

20,520 miles

$37,477

Fair Deal
Certified Pre-Owned
Milford, MA
31 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
20,520
Stock number:
TP6597
VIN:
5TDKDRBH0RS567405

Sponsored

2024 Toyota Highlander XLE AWD

2024 Toyota Highlander

XLE AWD

30,269 miles

$37,998

Good Deal
Certified Pre-Owned
Tewksbury, MA
45 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
30,269
Stock number:
TY105739R
VIN:
5TDKDRBH9RS538095

Sponsored

2020 Toyota Highlander Platinum AWD

2020 Toyota Highlander

Platinum AWD

54,003 miles

$33,799

Good Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Glazed Caramel
Transmission:
8-Speed Automatic
Mileage:
54,003
Stock number:
N27112C
VIN:
5TDFZRBH5LS041992

Sponsored

2023 Toyota Highlander XLE AWD

2023 Toyota Highlander

XLE AWD

62,094 miles

$33,333

Fair Deal
Certified Pre-Owned
Lancaster, MA
22 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
62,094
Stock number:
RXP1031
VIN:
5TDKDRBH6PS007630

2023 Toyota Highlander XSE AWD

2023 Toyota Highlander

XSE AWD

43,500 miles

$37,995

Fair Deal
Certified Pre-Owned
E Swanzey, NH
37 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
43,500
Stock number:
25IP002
VIN:
5TDKDRBH3PS509706

2023 Toyota Highlander XLE AWD

2023 Toyota Highlander

XLE AWD

34,244 miles

$35,798

Good Deal
Certified Pre-Owned
Tewksbury, MA
45 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
34,244
Stock number:
TY105756T
VIN:
5TDKDRBH5PS005190

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE AWD

54,280 miles

$31,999

Good Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
54,280
Stock number:
N25487T
VIN:
5TDHZRBH3NS594569

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

50,946 miles

$33,385

Good Deal
Certified Pre-Owned
Woburn, MA
48 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
50,946
Stock number:
N39377A
VIN:
5TDKDRBH0PS503751

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

XLE AWD

30,269 miles

$37,998

Good Deal
Certified Pre-Owned
Tewksbury, MA
45 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Pearl
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
30,269
Stock number:
TY105739R
VIN:
5TDKDRBH9RS538095

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE AWD

60,783 miles

$32,595

Fair Deal
Certified Pre-Owned
E Swanzey, NH
37 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
8-Speed Automatic
Mileage:
60,783
Stock number:
360072A
VIN:
5TDHZRBH2NS239957

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XSE AWD

41,536 miles

$37,899

Fair Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Wind Chill Pearl Off- White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
41,536
Stock number:
C4331
VIN:
5TDKDRBH1PS510790

Preparing for a close up...

Photos coming soon

2019 Toyota Highlander

XLE AWD

60,764 miles

$26,995

Fair Deal
Certified Pre-Owned
E Swanzey, NH
37 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
60,764
Stock number:
25LP061
VIN:
5TDJZRFH5KS603232

Preparing for a close up...

Photos coming soon

2017 Toyota Highlander

XLE AWD

77,772 miles

$22,489

Good Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blizzard Pearl White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
77,772
Stock number:
N27110C
VIN:
5TDJZRFH5HS455589

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

35,187 miles

$35,985

Fair Deal
Certified Pre-Owned
Woburn, MA
48 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Moon Dust
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
35,187
Stock number:
N39032A
VIN:
5TDKDRBH6PS501258

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE FWD

39,743 miles

$33,725

Good Deal
Certified Pre-Owned
Norwood, MA
45 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,743
Stock number:
U0300313
VIN:
5TDKDRAH5PS511071

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

XLE AWD

23,640 miles

$39,985

Fair Deal
Certified Pre-Owned
Woburn, MA
48 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
23,640
Stock number:
P17341
VIN:
5TDKDRBH8RS563263

Preparing for a close up...

Photos coming soon

2020 Toyota Highlander

Platinum AWD

54,003 miles

$33,799

Good Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Glazed Caramel
Transmission:
8-Speed Automatic
Mileage:
54,003
Stock number:
N27112C
VIN:
5TDFZRBH5LS041992

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

Limited AWD

35,529 miles

$37,798

Good Deal
Certified Pre-Owned
Tewksbury, MA
45 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
35,529
Stock number:
TY105778C
VIN:
5TDKDRBH7PS024999

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

LE AWD

53,236 miles

$29,995

Fair Deal
Certified Pre-Owned
E Swanzey, NH
37 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
53,236
Stock number:
25JP018
VIN:
5TDBZRBH8NS254890

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

Platinum AWD

52,508 miles

$36,911

Great Deal
Certified Pre-Owned
Northampton, MA
30 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
52,508
Stock number:
NS168870T
VIN:
5TDFZRBH8NS168870

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

Limited AWD

61,099 miles

$33,971

Good Deal
Certified Pre-Owned
Norwood, MA
45 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
8-Speed Automatic
Mileage:
61,099
Stock number:
U0300267
VIN:
5TDKDRBH6PS017896

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

LE AWD

20,520 miles

$37,477

Fair Deal
Certified Pre-Owned
Milford, MA
31 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
20,520
Stock number:
TP6597
VIN:
5TDKDRBH0RS567405

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

72,492 miles

$31,500

Good Deal
Certified Pre-Owned
Nashua, NH
40 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
72,492
Stock number:
N26309C
VIN:
5TDKDRBH6PS007983

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE AWD

30,772 miles

$35,997

Good Deal
Certified Pre-Owned
Hartford, CT
50 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Moon Dust
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,772
Stock number:
UP42820
VIN:
5TDKDRBH6PS002413

Sponsored

  1. Home
  2. / Certified Pre-Owned
  3. / Toyota Highlander
  4. / Massachusetts
  5. / Oakham
  • Toyota Highlander in Worcester MA

  • Toyota Highlander in Groton MA

  • Toyota Highlander in Chicopee MA

  • Toyota Highlander in Brattleboro VT

  • Toyota Highlander in Providence RI

  • Toyota Highlander in Boston MA

  • Toyota Highlander in Hartford CT

  • Toyota Highlander in Manchester NH

  • Toyota Highlander in Pittsfield MA

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.