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Pontiac Chieftain (1949 to 1958)

The Pontiac Chieftain was a series of cars first introduced in 1949. The Chieftain was available in a variety of body styles, and over the c...

The Pontiac Chieftain was a series of cars first introduced in 1949. The Chieftain was available in a variety of body styles, and over the course of its production was fitted with a variety of inlline 6, inline 8, and V8 engines. The Pontiac Chieftain was built in three generations: First Generation (1949-1954), Second Generation (1955-1957), and Third Generation (1958).

Pontiac Chieftain FAQs

Model years for Pontiac Chieftain (1949 to 1958)

For Sale 9

Avg $30,533

Sales Count 80

Dollar Volume $2.4m

Lowest Sale $2,200

Top Sale $134,750

Most Recent $18,500

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Showing 24 of 166 related listings

Indianapolis, IN, USA

1955 Pontiac Chieftain

Original & Highly Original

79k mi

Automatic

LHD

Sold

$15,000

Mecum

Oct 6, 2023

Details

SAVE

Lot F218: 1955 Pontiac Chieftain

Sold

$15,000

79,802 mi
Location: Indianapolis, IN, 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

Dallas, TX, USA

1958 Pontiac Chieftain

Original & Highly Original

35 mi

Automatic

LHD

Not Sold

$70,000

Mecum

Sep 23, 2023

Details

SAVE

Lot S157: 1958 Pontiac Chieftain

Not Sold

$70,000

35 mi
Location: Dallas, 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: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

1953 Pontiac Chieftan Deluxe Convertible

Shorewood Hills, WI, USA

1953 Pontiac Chieftan Deluxe Convertible

Original & Highly Original

94k mi TMU

Manual

LHD

Not Sold

$12,500

Bring a Trailer

Sep 7, 2023

Details

SAVE

Lot 119594: 1953 Pontiac Chieftan Deluxe Convertible

Not Sold

$12,500

94,000 mi TMU
Location: Shorewood Hills, WI, 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

Lee's Summit, MO, USA

1957 Pontiac Chieftain Two-Door Sedan

Custom

77k mi TMU

Automatic

LHD

Not Sold

$15,500

Bring a Trailer

Sep 7, 2023

Details

SAVE

Lot 119628: 1957 Pontiac Chieftain Two-Door Sedan

Not Sold

$15,500

77,000 mi TMU
Location: Lee's Summit, MO, 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

Moorpark, CA, USA

1956 Pontiac Chieftain

Original & Highly Original

2k mi TMU

Automatic

LHD

Not Sold

$20,810

Clasiq Auctions

Sep 6, 2023

Details

SAVE

Lot 1968: 1956 Pontiac Chieftain

Not Sold

$20,810

2,500 mi TMU
Location: Moorpark, 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: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

1953 Pontiac Chieftain Deluxe Station Wagon

Auburn, IN, USA

1953 Pontiac Chieftain Deluxe Station Wagon

Original & Highly Original

TMU

Automatic

LHD

Sold

$29,120

Worldwide Auctioneers

Sep 2, 2023

Details

SAVE

Lot 134: 1953 Pontiac Chieftain Deluxe Station Wagon

Sold

$29,120

TMU
Location: Auburn, IN, 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

Harrisburg, PA, USA

1955 Pontiac Chieftain

Original & Highly Original

99k mi

Automatic

LHD

Sold

$30,000

Mecum

Jul 27, 2023

Details

SAVE

Lot T40: 1955 Pontiac Chieftain

Sold

$30,000

99,643 mi
Location: Harrisburg, PA, 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

Harrisburg, PA, USA

1958 Pontiac Chieftain

Original & Highly Original

35k mi

Automatic

LHD

Sold

$18,000

Mecum

Jul 26, 2023

Details

SAVE

Lot W116.1: 1958 Pontiac Chieftain

Sold

$18,000

35,544 mi
Location: Harrisburg, PA, 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

Greensboro, NC, USA

1956 Pontiac Chieftain

Original & Highly Original

TMU

Automatic

LHD

Sold

$52,000

GAA

Jul 21, 2023

Details

SAVE

Lot FR0204: 1956 Pontiac Chieftain

Sold

$52,000

TMU
Location: Greensboro, 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

WEBSITE

Sioux City, IA, USA

1957 Pontiac Super Chief

Original & Highly Original

78 mi

Automatic

LHD

Last Asking

$49,500

Jensen Dealerships

Jun 1, 2023

Details

SAVE

Lot Q3235: 1957 Pontiac Super Chief

Last Asking

$49,500

78 mi
Location: Sioux City, IA, 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

Lithia Springs, GA, USA

1955 Pontiac Chieftain

Original & Highly Original

14k mi TMU

Automatic

LHD

Last Asking

$24,995

Streetside Classics

May 26, 2023

Details

SAVE

Lot 7097-ATL: 1955 Pontiac Chieftain

Last Asking

$24,995

13,960 mi TMU
Location: Lithia Springs, GA, 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

Sainte-Madeleine, QC, CAN

1951 Pontiac Fleetleader Deluxe 3-Speed

Original & Highly Original

72k mi TMU

Manual

LHD

Not Sold

$13,000

Hemmings

May 24, 2023

Details

SAVE

Lot 10005: 1951 Pontiac Fleetleader Deluxe 3-Speed

Not Sold

$13,000

72,551 mi TMU
Location: Sainte-Madeleine, QC, CAN
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

Indianapolis, IN, USA

1953 Pontiac Chieftan Wagon

Original & Highly Original

50k mi

Automatic

LHD

Not Sold

$35,000

Mecum

May 20, 2023

Details

SAVE

Lot S25: 1953 Pontiac Chieftan Wagon

Not Sold

$35,000

50,018 mi
Location: Indianapolis, IN, 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

Indianapolis, IN, USA

1955 Pontiac Chieftain

Custom

3k mi TMU

Automatic

LHD

Sold

$70,000

Mecum

May 20, 2023

Details

SAVE

Lot S178: 1955 Pontiac Chieftain

Sold

$70,000

3,023 mi TMU
Location: Indianapolis, IN, 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

1957 Pontiac Chieftain Safari Two-Door Station Wagon

Salinas, CA, USA

1957 Pontiac Chieftain Safari Two-Door Station Wagon

Original & Highly Original

5k mi

Automatic

LHD

Sold

$25,410

Hemmings

May 20, 2023

Details

SAVE

Lot 3459-PC: 1957 Pontiac Chieftain Safari Two-Door Station Wagon

Sold

$25,410

5,334 mi
Location: Salinas, 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: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Glastonbury, CT, USA

1955 Pontiac Chieftain 2 Door Hardtop

Original & Highly Original

64k mi

Automatic

LHD

Sold

$16,800

Hemmings

May 20, 2023

Details

SAVE

Lot 8492-PC: 1955 Pontiac Chieftain 2 Door Hardtop

Sold

$16,800

64,422 mi
Location: Glastonbury, CT, 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

Indianapolis, IN, USA

1950 Pontiac Chieftain Convertible

Original & Highly Original

56k mi TMU

Automatic

LHD

Sold

$31,000

Mecum

May 18, 2023

Details

SAVE

Lot T258: 1950 Pontiac Chieftain Convertible

Sold

$31,000

55,994 mi TMU
Location: Indianapolis, IN, 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

Indianapolis, IN, USA

1956 Pontiac Chieftain

Modified

64k mi TMU

Automatic

LHD

Sold

$18,500

Mecum

May 14, 2023

Details

SAVE

Lot L186: 1956 Pontiac Chieftain

Sold

$18,500

64,447 mi TMU
Location: Indianapolis, IN, 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

Plymouth, MI, USA

1953 Pontiac Chieftain Convertible

Original & Highly Original

3k mi TMU

Automatic

LHD

Last Asking

$109,900

Vanguard Motor Sales

May 14, 2023

Details

SAVE

Lot 8XH51330: 1953 Pontiac Chieftain Convertible

Last Asking

$109,900

3,591 mi TMU
Location: Plymouth, MI, 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

Grand Rapids, MI, USA

1951 Pontiac Chieftain Deluxe

Original & Highly Original

46k mi

Automatic

LHD

Last Asking

$27,900

GR Auto Gallery

May 14, 2023

Details

SAVE

Lot P5541J: 1951 Pontiac Chieftain Deluxe

Last Asking

$27,900

46,164 mi
Location: Grand Rapids, MI, 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

1953 Pontiac Chieftain Deluxe Convertible

Torrance, CA, USA

1953 Pontiac Chieftain Deluxe Convertible

Original & Highly Original

70k mi

Automatic

LHD

Last Asking

$49,500

West Coast Classics

May 12, 2023

Details

SAVE

Lot XH43755: 1953 Pontiac Chieftain Deluxe Convertible

Last Asking

$49,500

70,409 mi
Location: Torrance, 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: Automatic
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Sainte-Madeleine, QC, CAN

1951 Pontiac Fleetleader Deluxe 3-Speed

Original & Highly Original

72k mi TMU

Manual

LHD

Not Sold

PCARMARKET

Apr 26, 2023

Details

SAVE

Lot 0029001-DT: 1951 Pontiac Fleetleader Deluxe 3-Speed

Not Sold

72,550 mi TMU
Location: Sainte-Madeleine, QC, CAN
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

Sainte-Madeleine, QC, CAN

1951 Pontiac Fleetleader Deluxe 3-Speed

Original & Highly Original

72k mi TMU

Manual

LHD

Not Sold

$15,000

PCARMARKET

Apr 26, 2023

Details

SAVE

Lot 0029001: 1951 Pontiac Fleetleader Deluxe 3-Speed

Not Sold

$15,000

72,550 mi TMU
Location: Sainte-Madeleine, QC, CAN
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

1950 Pontiac Chieftain Silver 8 Streak Streamliner

Germany

1950 Pontiac Chieftain Silver 8 Streak Streamliner

Original & Highly Original

37k mi

Automatic

LHD

Not Sold

€12,500

Catawiki

Apr 24, 2023

Details

SAVE

Lot 69362671: 1950 Pontiac Chieftain Silver 8 Streak Streamliner

Not Sold

€12,500 ($13,788)

37,586 mi
Location: Germany
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