Highwaymen Paintings

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NORMAN WRIGHT FLORIDA ARTIST THE TEMPEST: Wright, Norman "N.E." Florida Artist - Highwaymen style painting. Oil on Masonite - signed lower right. Executed in brushwork. A vibrant shoreline trembles under the force of an approaching storm. Cre

5 days Left

NORMAN WRIGHT FLORIDA ARTIST THE TEMPEST

(1 bid)

HEZEKIAH BAKER JR FLORIDA ARTIST BLUE INLET: Baker Jr, Hezekiah - Florida Artist Highwaymen style painting. Son of Highwaymen Hezekiah Baker. Oil on Masonite - signed lower right and verso. Executed in brush and palette knife. An exceptionally w

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HEZEKIAH BAKER JR FLORIDA ARTIST BLUE INLET

NORMAN WRIGHT FLORIDA ARTIST BEACH SCENE: Wright, Norman "N.E." Florida Artist - Highwaymen style painting. Oil on Board - signed lower left. Norman Wright’s small-scale seascape distills Florida's coastal lyricism into an intimate stud

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NORMAN WRIGHT FLORIDA ARTIST BEACH SCENE

1967 James Gibson Florida Highwayman "At Dusk in the Swamp"Painting on Upson Board: 1967 James Gibson Florida Highwayman At Dusk in the Swamp Painting on Upson Board. James Gibson (1938 - 2017) is an American landscape artist from Moore Haven, Florida and one of the original 26 Flori

Jul 19, 2026

1967 James Gibson Florida Highwayman "At Dusk in the Swamp"Painting on Upson Board

(8 bids)

Livingston Roberts 1941-2004 Highwayman Painting: Livingstone (Castro) Roberts (American, 1941-2004), oil on Upson board featuring a tropical coastal landscape with two wind-swept palm trees overlooking blue waters beneath a softly clouded sky. Paint

Jun 17, 2026

Livingston Roberts 1941-2004 Highwayman Painting

Hill Auction Gallery

(4 bids)

James Gibson Florida Highwayman Large Night Palms Painting on Upson Board: James Gibson Florida Highwayman Large Night Palms Painting on Upson Board. James Gibson (1938 - 2017) is an American landscape artist from Moore Haven, Florida and one of the original 26 Florida Highw

Jul 19, 2026

James Gibson Florida Highwayman Large Night Palms Painting on Upson Board

(4 bids)

Isaac Knight 1941-2022 Florida Highwayman Painting: Isaac Knight (American, 1941-2022), oil painting on board depicting a tranquil Florida landscape with tall trees reflected along calm waters beneath a dramatic cloud-filled sky. Signed lower right I.

Jun 17, 2026

Isaac Knight 1941-2022 Florida Highwayman Painting

Hill Auction Gallery

(2 bids)

Sam Newton (1948-2019) American, Oil on Canvas Florida Highwaymen Landscape: Sam Newton (1948-2019) American, Oil on Canvas Florida Highwaymen Landscape. Vibrant Florida landscape depicting a lush, atmospheric marsh scene featuring towering palms, wading birds, and a dramatic,

Jun 13, 2026

Sam Newton (1948-2019) American, Oil on Canvas Florida Highwaymen Landscape

Sarasota Estate Auction

Framed Highwayman 2nd Generation FLA Landscape on Board signed T. Newton: Framed Highwayman 2nd Generation FLA Landscape on Board signed T. Newton. Tracy Newton is a second-generation Florida Highwaymen artist and the son of original Hall of Fame Highwayman, Sam Newton. He

Jul 19, 2026

Framed Highwayman 2nd Generation FLA Landscape on Board signed T. Newton

(3 bids)

Isaac Knight 1941-2022 Florida Highwayman Painting: Oil on masonite board painting attributed to Isaac Knight (American; Florida, 1941-2022), depicting a stylized tropical landscape centered by a flamboyant poinsettia tree with vivid red foliage set be

Jun 17, 2026

Isaac Knight 1941-2022 Florida Highwayman Painting

Hill Auction Gallery

(3 bids)

Harold Newton was an American landscape artist. He was a founding member of the Florida Highwaymen,: Harold Newton was an American landscape artist. He was a founding member of the Florida Highwaymen, a group of fellow African American landscape artists. Newton and the other Highwaymen were influence

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Harold Newton was an American landscape artist. He was a founding member of the Florida Highwaymen,

MJ Auction Gallery LLC

WILLIE REYNOLDS FLORIDA ARTIST ANOTHER HALFWAYMEN: Reynolds, Willie "Po' Boy" - Florida Artist Painting. Oil on Upson - signed lower right. Executed in brush and palette knife. Willie was among the lesser-known artists associated with the Florida High

5 days Left

WILLIE REYNOLDS FLORIDA ARTIST ANOTHER HALFWAYMEN

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Willie Daniels, Oil on Canvas, American (1951 - 2021): Artist, Year: Willie Daniels, (1951 - 2021). Origin: American. Medium: Oil on Canvas. Dimensions: 19.5" x 15.5"; 27" x 23". Condition: Excellent. Provenance: IN PRIVATE COLLECTION. From the Estate of

3 days Left

Willie Daniels, Oil on Canvas, American (1951 - 2021)

Lucky's International LLC

Raymond Plockelman (American, 1943–2021) Florida Oil On Board Painting: Raymond Plockelman (American, 1943–2021) Florida Oil On Board Painting 20th Cent., American This oil-on-board landscape by Florida native Raymond Plockelman captures a windswept coastal seascape hea

Jun 16, 2026

Raymond Plockelman (American, 1943–2021) Florida Oil On Board Painting

Akiba Galleries

(2 bids)

MARK STANFORD FLORIDA ARTIST ORANGE GROVE: Stanford, Mark - Florida Artist painting. Oil on artist board - signed lower right. A crane walks along the canal amongst the orange groves. Board measures 16x20 framed to overall size of 21x25. Mark

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MARK STANFORD FLORIDA ARTIST ORANGE GROVE

Libby Hobson (20th Century) American, South Carolina Landscape Oil on Canvas: Libby Hobson (20th Century) American, South Carolina Landscape Oil on Canvas. Showcases the regional artist's self-taught style similar to the Florida Highwaymen, capturing the dream-like deep swa

Jun 14, 2026

Libby Hobson (20th Century) American, South Carolina Landscape Oil on Canvas

Sarasota Estate Auction

TODD MARTIN FLORIDA ARTIST WABASSO WESTERLY SUNSET: Martin, Todd - Florida Legacy Artist Painting. Oil on Canvas Board - signed lower right. Executed in brush and palette knife . Todd Martin’s Wabasso sunset looks back toward the mainland, palm t

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TODD MARTIN FLORIDA ARTIST WABASSO WESTERLY SUNSET

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