Highwaymen Paintings

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Al Black (1947-2025) American, Oil on Canvas Florida Highwaymen Landscape Painting: Al Black (1947-2025) American, Oil on Canvas Florida Highwaymen Landscape Painting. Quintessential Florida Highwayman oil painting featuring a serene coastal scene with a lone fisherman in a boat

Jun 13, 2026

Al Black (1947-2025) American, Oil on Canvas Florida Highwaymen Landscape Painting

Sarasota Estate Auction

Very Large Florida Highwaymen Isaac Knight FL Oil on Board Painting w/ Strong Provenance: Described By: Dillon DT67261 NOYDD Title: Very Large Florida Highwaymen Isaac Knight FL Oil on Board Painting w/ Strong Provenance Description: Very Large Florida Highwaymen Isaac Knight FL Oil on Boa

Jun 11, 2026

Very Large Florida Highwaymen Isaac Knight FL Oil on Board Painting w/ Strong Provenance

Hess Fine Auctions

(9 bids)

ALPHONSO MORAN FLORIDA HIGHWAYMEN MASTERFUL MORAN: Moran, Alfonso Alfonzo Alphonso “Poncho” (1930-2003) Florida Highwaymen Painting. Oil on Orange Peel Upson - signed lower right. Executed in brush and palette knife. Alfonso Moran—ra

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ALPHONSO MORAN FLORIDA HIGHWAYMEN MASTERFUL MORAN

HAROLD NEWTON FLORIDA HIGHWAYMEN TEMPESTUOUS RIO: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in Palette Knife on a field of Brushwork. With precious few finer, Harold Newton’s classic sout

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HAROLD NEWTON FLORIDA HIGHWAYMEN TEMPESTUOUS RIO

HAROLD NEWTON FLORIDA HIGHWAYMEN EPIPHANIC MOMENT: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Upson - signed lower right. Harold Newton’s radiant “God Sky” erupts as sunlight bursts through storm-torn clouds, igni

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HAROLD NEWTON FLORIDA HIGHWAYMEN EPIPHANIC MOMENT

MARY ANN CARROLL FLORIDA HIGHWAYMEN PUBLISHED GEM: Carroll, Mary Ann (1940-2019) Florida Highwaymen Painting. Oil on Masonite - signed lower left. Featured in "Mary Ann Carroll First Lady Of The Highwaymen" book by Gary Monroe. Executed in brush and p

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MARY ANN CARROLL FLORIDA HIGHWAYMEN PUBLISHED GEM

(1 bid)

GEORGE BUCKNER FLORIDA HIGHWAYMEN MASTERPIECE: Buckner, George (1942-2002) Florida Highwaymen Painting. Oil on Canvas - signed lower right. Executed in brush. George Buckner’s composition unfurls beneath billowing cumulus clouds rendered wit

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GEORGE BUCKNER FLORIDA HIGHWAYMEN MASTERPIECE

(1 bid)

SAM NEWTON FLORIDA HIGHWAYMEN CREPUSCULAR STORM: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Orange Peel Upson - signed lower right. Executed in palette knife and brush. Sam plunges the viewer into a storm-charged night, where black

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SAM NEWTON FLORIDA HIGHWAYMEN CREPUSCULAR STORM

R.A. MCLENDON FLORIDA HIGHWAYMEN CYPRESS MARSH: McLendon, R.A. “Roy” (1932-2024) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed with brush and palette knife. Moonlight casts a cool, silvery glow across the cypr

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R.A. MCLENDON FLORIDA HIGHWAYMEN CYPRESS MARSH

(1 bid)

HAROLD NEWTON FLORIDA HIGHWAYMEN POINCIANA: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Transitional Masonite - signed lower right. Executed in brush and palette knife. Harold Newton’s scarce Poinciana—fewer than

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HAROLD NEWTON FLORIDA HIGHWAYMEN POINCIANA

JAMES GIBSON FLORIDA HIGHWAYMEN JAMAICAN MOUNTAINS: Gibson, James (1938-2017) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in Knife. Gibson’s rare Jamaican landscape reveals his distinct voice within the Highwaymen

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JAMES GIBSON FLORIDA HIGHWAYMEN JAMAICAN MOUNTAINS

LEMUEL NEWTON FLORIDA HIGHWAYMEN TRILOGY EMBRACE: Newton, Lemuel (1950-2014) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette knife. Exceedingly rare Fire Sky presents a sun-drenched Florida wetland oasis where a bl

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LEMUEL NEWTON FLORIDA HIGHWAYMEN TRILOGY EMBRACE

R.A. MCLENDON FLORIDA HIGHWAYMEN RIVER STUDY: McLendon, R.A. “Roy” (1932-2024) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette and brush. R.A. McLendon distills the Highwaymen ethos into this small,

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R.A. MCLENDON FLORIDA HIGHWAYMEN RIVER STUDY

(1 bid)

HAROLD NEWTON FLORIDA HIGHWAYMEN OCEANS MEETING: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Transitional Masonite - signed lower right. Harold Newton’s vision of Fort Pierce’s river mouth becomes uniquely seamless, th

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HAROLD NEWTON FLORIDA HIGHWAYMEN OCEANS MEETING

HAROLD NEWTON FLORIDA HIGHWAYMEN SOUTH FORK: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Transitional Masonite - signed lower right. Executed in palette knife upon a field of brushwork. Harold Newton’spainting of a misty

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HAROLD NEWTON FLORIDA HIGHWAYMEN SOUTH FORK

ELLIS BUCKNER FLORIDA HIGHWAYMEN ROYAL POINCIANA: Buckner, Ellis (1943-1991) Florida Highwaymen Painting. Oil on orange peel Upson - signed lower right. Executed in pallet knife. This early Ellis Buckner painting offers a rare glimpse into the Florid

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ELLIS BUCKNER FLORIDA HIGHWAYMEN ROYAL POINCIANA

ALFRED HAIR FLORIDA HIGHWAYMEN RIVER SOLACE: Hair, Alfred (1941-1970) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette knife upon a field of brushwork. This early, best in class-production Alfred Hair work is h

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ALFRED HAIR FLORIDA HIGHWAYMEN RIVER SOLACE

(1 bid)

HAROLD NEWTON FLORIDA HIGHWAYMEN NUMINOUS SPLENDOR: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette knife and brush work. Newton unveils a masterful golden dawn along the South Fork as it m

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HAROLD NEWTON FLORIDA HIGHWAYMEN NUMINOUS SPLENDOR

ELLIS BUCKNER FLORIDA HIGHWAYMEN SAND PAINT FRAME: Buckner, Ellis (1943-1991) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in brush and palette knife. An early moonlit St. Lucie River scene glows with quiet mystery. An asso

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ELLIS BUCKNER FLORIDA HIGHWAYMEN SAND PAINT FRAME

JOHNNY DANIELS FLORIDA HIGHWAYMEN SUNRISE SOLACE: Daniels, Johnny (1954-2009) Florida Highwaymen Painting. Oil on Canvas - signed lower right. Executed in Brush and palette knife. Johnny Daniels captures golden-hour sunrise along the South Fork of th

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JOHNNY DANIELS FLORIDA HIGHWAYMEN SUNRISE SOLACE

(1 bid)

JAMES GIBSON FLORIDA HIGHWAYMEN DANCING PALMS: Gibson, James (1938-2017) Florida Highwaymen Painting. Oil on Orange Peel Upson - signed lower right. Executed in full palette knife. A rare full signature Gibson in very early large-format. The visio

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JAMES GIBSON FLORIDA HIGHWAYMEN DANCING PALMS

MARY ANN CARROLL FLORIDA HIGHWAYMEN MATRIARCH 2018: Carroll, Mary Ann (1940-2019) Florida Highwaymen Painting. Oil on Canvas - signed lower right and verso. Executed in brush. Mary Ann Carroll’s late-period wetland vignette unfolds beneath blue,

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MARY ANN CARROLL FLORIDA HIGHWAYMEN MATRIARCH 2018

WILLIE REAGAN FLORIDA HIGHWAYMEN PEEKSKILL NY: Reagan, Willie C. (1939-2026) Florida Highwaymen Painting. Oil on Upson - signed lower right and verso. Executed in palette knife and brush. Reagan re imagines Peekskill's fall brilliance through a Hi

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WILLIE REAGAN FLORIDA HIGHWAYMEN PEEKSKILL NY

ALFRED HAIR FLORIDA HIGHWAYMEN TOUCH THE FIRE: Hair, Alfred (1941-1970) Florida Highwaymen Painting. Oil on Linen Upson - signed lower right. Executed in brush and palette knife. Hair’s fiery vision ignites as a vibrant fire-sky pours its in

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ALFRED HAIR FLORIDA HIGHWAYMEN TOUCH THE FIRE

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