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Oldsmobile 442 - 1st Gen (1964 to 1967)

Oldsmobile introduced the 442 performance package in 1964. The 442 featured various improvements over the F-85 and Cutlass upon which it was...

Oldsmobile introduced the 442 performance package in 1964. The 442 featured various improvements over the F-85 and Cutlass upon which it was based. The first generation of 442 was available as a coupe, convertible, or sedan, and was offered with a 5.4L or 6.6L V8 engine. Production of the first generation 442 ended in 1967, when it was replaced by the Second Generation Oldsmobile 442.

Oldsmobile 442 - 1st Gen FAQs

Model years for Oldsmobile 442 - 1st Gen (1964 to 1967)

For Sale 12

Avg $43,010

Sales Count 90

Dollar Volume $3.9m

Lowest Sale $10,500

Top Sale $121,000

Most Recent $70,000

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Showing 24 of 204 related listings

Los Angeles, California, USA

1966 Oldsmobile 442 Pro-Touring Coupe

Custom

12k mi TMU

Automatic

LHD

For Sale

$64,900

Hemmings

Jul 22, 2024

Details

SAVE

Lot 19979-PC: 1966 Oldsmobile 442 Pro-Touring Coupe

For Sale

$64,900

12,600 mi TMU
Location: Los Angeles, California, USA
Originality:
Custom

Highly modified and/or Restored vehicles with uprated, non-period correct engine swaps, or engines from outside the original manufacturer, and/or vehicles with significant body customizations or conversions. Generally, Custom vehicles cannot be easily returned to their original factory specifications.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Lehman Township, Pennsylvania, USA

1967 Oldsmobile 442 Holiday Coupe

Original & Highly Original

9k mi TMU

Manual

LHD

For Sale

$26,250

Hemmings

Jul 16, 2024

Details

SAVE

Lot 20101-PC: 1967 Oldsmobile 442 Holiday Coupe

For Sale

$26,250

9,886 mi TMU
Location: Lehman Township, Pennsylvania, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Nashville, Illinois, USA

1966 Oldsmobile Cutlass 442

Original & Highly Original

78k mi

Automatic

LHD

For Sale

$39,900

Vaughn's Classic Cars

Jul 6, 2024

Details

SAVE

Lot VCC317: 1966 Oldsmobile Cutlass 442

For Sale

$39,900

78,930 mi
Location: Nashville, Illinois, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Fullerton, California, USA

1966 Oldsmobile 442 490CI V8

Modified

TMU

Automatic

LHD

For Sale

$83,000

Hemmings

Jun 27, 2024

Details

SAVE

Lot 16872-PC: 1966 Oldsmobile 442 490CI V8

For Sale

$83,000

TMU
Location: Fullerton, California, USA
Originality:
Modified

Vehicles with a period-correct engine and body, with multiple removable modifications, or a few significant modifications such as increased displacement, added performance equipment (turbo, supercharger, headers), transmission swaps, bumpers, or body wraps. Modified vehicles can generally be returned to original factory specifications.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Cook County, Illinois, USA

1966 Oldsmobile 442

Original & Highly Original

47k mi TMU

Manual

LHD

For Sale

$56,900

Midwest Car Exchange

Jun 2, 2024

Details

SAVE

Lot 299372: 1966 Oldsmobile 442

For Sale

$56,900

47,153 mi TMU
Location: Cook County, Illinois, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Mankato, Minnesota, USA

1967 Oldsmobile 442 Convertible

Original & Highly Original

11k mi

Automatic

LHD

For Sale

$44,900

Unique Classic Cars

May 23, 2024

Details

SAVE

Lot 7341: 1967 Oldsmobile 442 Convertible

For Sale

$44,900

11,630 mi
Location: Mankato, Minnesota, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Englewood, Colorado, USA

1965 Oldsmobile Cutlass 442

Original & Highly Original

40k mi TMU

Automatic

LHD

For Sale

$65,900

Cars Remember When

Apr 28, 2024

Details

SAVE

Lot O0580: 1965 Oldsmobile Cutlass 442

For Sale

$65,900

40,032 mi TMU
Location: Englewood, Colorado, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Plainfield, Indiana, USA

1965 Oldsmobile Cutlass 442 Convertible

Original & Highly Original

23k mi TMU

Manual

LHD

For Sale

$35,900

GR Auto Gallery

Apr 23, 2024

Details

SAVE

Lot BIN577: 1965 Oldsmobile Cutlass 442 Convertible

For Sale

$35,900

23,400 mi TMU
Location: Plainfield, Indiana, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Concord, NC, USA

1967 Oldsmobile 442

Original & Highly Original

91k mi TMU

Automatic

LHD

For Sale

$43,995

Streetside Classics

Apr 20, 2024

Details

SAVE

Lot 8034-CHA: 1967 Oldsmobile 442

For Sale

$43,995

90,971 mi TMU
Location: Concord, NC, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

North Andover, MA, USA

1966 Oldsmobile Cutlass 442

Original & Highly Original

17k mi TMU

Manual

LHD

For Sale

$65,900

Silverstone Motorcars

Mar 22, 2024

Details

SAVE

Lot 1001059: 1966 Oldsmobile Cutlass 442

For Sale

$65,900

17,537 mi TMU
Location: North Andover, MA, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

San Jose, CA, USA

1965 Oldsmobile 442

Original & Highly Original

36k mi TMU

Manual

LHD

For Sale

$41,900

American Motors Custom & Classics

Mar 14, 2024

Details

SAVE

Lot AM4656: 1965 Oldsmobile 442

For Sale

$41,900

36,422 mi TMU
Location: San Jose, CA, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Harrisburg, Pennsylvania, USA

1965 Oldsmobile 442 Convertible

Original & Highly Original

17k mi TMU

Manual

LHD

Not Sold

$40,000

Mecum

Jul 26, 2024

Details

SAVE

Lot F99: 1965 Oldsmobile 442 Convertible

Not Sold

$40,000

17,640 mi TMU
Location: Harrisburg, Pennsylvania, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Harrisburg, Pennsylvania, USA

1964 Oldsmobile 442 Hardtop

Original & Highly Original

51k mi TMU

Manual

LHD

Not Sold

$40,000

Mecum

Jul 26, 2024

Details

SAVE

Lot F100: 1964 Oldsmobile 442 Hardtop

Not Sold

$40,000

51,231 mi TMU
Location: Harrisburg, Pennsylvania, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Greensboro, North Carolina, USA

1965 Oldsmobile 442 Convertible

Original & Highly Original

38k mi

Manual

LHD

Sold

$70,000

GAA

Jul 26, 2024

Details

SAVE

Lot FR0012: 1965 Oldsmobile 442 Convertible

Sold

$70,000

38,268 mi
Location: Greensboro, North Carolina, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Greensboro, North Carolina, USA

1965 Oldsmobile 442

Original & Highly Original

60k mi TMU

Automatic

LHD

Not Sold

$32,500

GAA

Jul 26, 2024

Details

SAVE

Lot FR0015: 1965 Oldsmobile 442

Not Sold

$32,500

60,215 mi TMU
Location: Greensboro, North Carolina, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

1965 Oldsmobile Cutlass 442 Holiday Coupe

Peoria, Illinois, USA

1965 Oldsmobile Cutlass 442 Holiday Coupe

Original & Highly Original

819 mi TMU

Manual

LHD

Sold

$29,000

Bring a Trailer

Jul 26, 2024

Details

SAVE

Lot 155939: 1965 Oldsmobile Cutlass 442 Holiday Coupe

Sold

$29,000

819 mi TMU
Location: Peoria, Illinois, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Harrisburg, Pennsylvania, USA

1965 Oldsmobile 442

Original & Highly Original

39k mi

Automatic

LHD

Not Sold

$32,000

Mecum

Jul 25, 2024

Details

SAVE

Lot T154: 1965 Oldsmobile 442

Not Sold

$32,000

39,120 mi
Location: Harrisburg, Pennsylvania, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Fort Worth, TX, USA

1965 Oldsmobile Cutlass 442

Original & Highly Original

58k mi TMU

Manual

LHD

Last Asking

$31,995

Streetside Classics

Jul 20, 2024

Details

SAVE

Lot 6589-DFW: 1965 Oldsmobile Cutlass 442

Last Asking

$31,995

58,392 mi TMU
Location: Fort Worth, TX, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Lehman Township, Pennsylvania, USA

1967 Oldsmobile 442 Holiday Coupe

Original & Highly Original

9k mi TMU

Manual

LHD

Not Sold

$10,750

Hemmings

Jul 15, 2024

Details

SAVE

Lot 20101: 1967 Oldsmobile 442 Holiday Coupe

Not Sold

$10,750

9,886 mi TMU
Location: Lehman Township, Pennsylvania, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Ruskin, FL, USA

1967 Oldsmobile 442 W-30

Modified

15k mi TMU

Manual

LHD

Pending

Gateway Classic Cars

Jul 5, 2024

Details

SAVE

Lot TPA2704: 1967 Oldsmobile 442 W-30

Pending

15,123 mi TMU
Location: Ruskin, FL, USA
Originality:
Modified

Vehicles with a period-correct engine and body, with multiple removable modifications, or a few significant modifications such as increased displacement, added performance equipment (turbo, supercharger, headers), transmission swaps, bumpers, or body wraps. Modified vehicles can generally be returned to original factory specifications.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Largo, Florida, USA

1966 Oldsmobile 442

Original & Highly Original

TMU

Automatic

LHD

Last Asking

$39,900

SuperSport Classics

Jul 4, 2024

Details

SAVE

Lot 2125: 1966 Oldsmobile 442

Last Asking

$39,900

TMU
Location: Largo, Florida, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Fort Worth, Texas, USA

1967 Oldsmobile 442 Convertible

Original & Highly Original

12k mi TMU

Manual

LHD

Last Asking

$47,995

Streetside Classics

Jun 30, 2024

Details

SAVE

Lot 6722-DFW: 1967 Oldsmobile 442 Convertible

Last Asking

$47,995

12,909 mi TMU
Location: Fort Worth, Texas, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

San Rafael, California, USA

1966 Oldsmobile 442 Holiday Coupe

Modified

47k mi

Automatic

LHD

Not Sold

$31,000

Bring a Trailer

Jun 21, 2024

Details

SAVE

Lot 151576: 1966 Oldsmobile 442 Holiday Coupe

Not Sold

$31,000

47,777 mi
Location: San Rafael, California, USA
Originality:
Modified

Vehicles with a period-correct engine and body, with multiple removable modifications, or a few significant modifications such as increased displacement, added performance equipment (turbo, supercharger, headers), transmission swaps, bumpers, or body wraps. Modified vehicles can generally be returned to original factory specifications.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Fenton, Missouri, USA

1965 Oldsmobile 442

Original & Highly Original

7k mi TMU

Manual

LHD

Sold

$10,500

Bring a Trailer

Jun 18, 2024

Details

SAVE

Lot 151199: 1965 Oldsmobile 442

Sold

$10,500

7,000 mi TMU
Location: Fenton, Missouri, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Manual
Driver side: LHD