Highwaymen Paintings

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AL BLACK FLORIDA HIGHWAYMEN SUNRISE RIVER: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. This luminous river scene captures the fragile stillness of sunrise

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN SUNRISE RIVER

(1 bid)

JAMES GIBSON FLORIDA HIGHWAYMEN MONOCHROMATIC: Gibson, James (1938 - 2017) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in pallet knife. Rendered in a restrained monochrome palette, this river scene evokes the atmospher

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN MONOCHROMATIC

JAMES GIBSON FLORIDA HIGHWAYMEN MOONLIT INLET: Gibson, James (1938-2017) Florida Highwaymen Painting. Oil on Transitional Masonite - signed lower right. Executed in brush and palette knife. Moonlit inlet study distills his gift for atmospheric res

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN MOONLIT INLET

CHICO WHEELER FLORIDA HIGHWAYMEN POINCIANA: Wheeler, Charles “Chico” (1946-2019) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed with brush and palette knife. A full-bloom Royal Poinciana commands this ni

Apr 25, 2026

CHICO WHEELER FLORIDA HIGHWAYMEN POINCIANA

AL BLACK FLORIDA HIGHWAYMEN SUNSET RIVER SCENE: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. This atmospheric Florida river scene captures dusk's fleeting lumino

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN SUNSET RIVER SCENE

SAM NEWTON FLORIDA HIGHWAYMEN UNTOUCHED PARADISE: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed with brush and palette knife. In this river scene, water and sky merge in a seamless tonal gradient,

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN UNTOUCHED PARADISE

SAM NEWTON FLORIDA HIGHWAYMEN SAIL AWAY: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed with brush and palette knife. A small sailboat glides along the river beneath a pale lavender sky th

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN SAIL AWAY

JAMES GIBSON FLORIDA HIGHWAYMEN MOONLIT RIVER: Gibson, James (1938-2017) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in pallet knife. In this moonlit Florida riverscape, a solitary palm leans over the softly shifting r

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN MOONLIT RIVER

HAROLD NEWTON FLORIDA HIGHWAYMEN PEACEFUL RIVER: Newton, Harold (1934-1994) Florida Highwaymen Painting. Oil on Masonite - signed lower middle. Executed in pallet knife. The painting evokes a serene atmospheric study, its mist-laden river dissolving

Apr 25, 2026

HAROLD NEWTON FLORIDA HIGHWAYMEN PEACEFUL RIVER

Al Black, Florida Highwaymen Painting, 24 x 36 — Nothing He Can Do Now: Florida Highwaymen Painting Al Black Oil on Early Upson Board Frame Dimensions 27 x 39 inches Painting Dimensions 24 x 36 inches This one settles into a real moment. A rare Al Black scene with a figur

May 02, 2026

Al Black, Florida Highwaymen Painting, 24 x 36 — Nothing He Can Do Now

Florida Highwaymen Auctions LLC

SAM NEWTON FLORIDA HIGHWAYMEN WETLAND SUNSET: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette knife. The painting captures a radiant sunset where orange, pink, yellow, and violet sweep a

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN WETLAND SUNSET

ALFRED HAIR FLORIDA HIGHWAYMEN MOONLIT COAST: Hair, Alfred (1941-1970) Florida Highwaymen Painting. Oil on Upson - signed lower right and autographed on verso by Doretha Hair & Roderick Hair. Executed in palette knife. This work exemplifies Hair&

Apr 25, 2026

ALFRED HAIR FLORIDA HIGHWAYMEN MOONLIT COAST

SAM NEWTON FLORIDA HIGHWAYMEN MOONLIT OCEAN: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in palette knife. Moonlight washes this vintage Sam Newton shoreline with a quiet, silver radiance, ill

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN MOONLIT OCEAN

HEZEKIAH BAKER FLORIDA HIGHWAYMEN RENEWAL RIVER: Baker, Hezekiah (1940-2007) Florida Highwaymen Painting. Oil on Fredrix Canvas Board - signed lower left. Executed in pallet knife. Baker’s canvas reveals his mastery of Florida’s wetlands

Apr 25, 2026

HEZEKIAH BAKER FLORIDA HIGHWAYMEN RENEWAL RIVER

Al Black, Florida Highwaymen Painting, 16 x 20 — Purple Fade, Golden Water: Florida Highwaymen Painting Al Black Oil on Canvas Board Frame Dimensions: 23 x 19 inches Painting Dimensions: 16 x 20 inches A color-driven sunset composition built around a soft leftward fade, where

May 02, 2026

Al Black, Florida Highwaymen Painting, 16 x 20 — Purple Fade, Golden Water

Florida Highwaymen Auctions LLC

(1 bid)

Al Black, Florida Highwaymen Painting, 16 x 20 — Crosswater Jacaranda Glow: Florida Highwaymen Painting Al Black Oil on Canvas Frame Dimensions: 23 x 19 inches Painting Dimensions: 16 x 20 inches A crosswater composition centered on a fully opened jacaranda, its violet canopy

May 02, 2026

Al Black, Florida Highwaymen Painting, 16 x 20 — Crosswater Jacaranda Glow

Florida Highwaymen Auctions LLC

(1 bid)

AL BLACK FLORIDA HIGHWAYMEN RAINBOW SKIES: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. A radiant spectrum sweeps across the sky, casting the river scene in

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN RAINBOW SKIES

(1 bid)

RODNEY DEMPS FLORIDA HIGHWAYMEN RIVER PALMS: Demps, Rodney (1953 - 2020) Florida Highwaymen Painting. Oil on Masonite - signed lower left. Executed in brush. This abstract Florida river scene distills the region's kinetic energy into rhythmic fo

Apr 25, 2026

RODNEY DEMPS FLORIDA HIGHWAYMEN RIVER PALMS

(1 bid)

Harold Newton, Florida Highwaymen Painting, 24 x 32 — Before Anything Moves: Florida Highwaymen Painting Harold Newton Oil on Masonite Frame Dimensions 28 x 36 inches Painting Dimensions 24 x 32 inches This one settles in before anything has a chance to start. A quiet spoil is

May 02, 2026

Harold Newton, Florida Highwaymen Painting, 24 x 32 — Before Anything Moves

Florida Highwaymen Auctions LLC

(1 bid)

AL BLACK FLORIDA HIGHWAYMEN 1 OF 2 RIVER SCENE: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. One of a paired river studies, this work presents aluminous turquois

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN 1 OF 2 RIVER SCENE

JAMES GIBSON FLORIDA HIGHWAYMEN BLUE MONOCHROME: Gibson, James (1938 - 2017) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in pallet knife. In this monochromatic Gibson composition, deep blues dissolve into velvety blacks,

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN BLUE MONOCHROME

WILLIE DANIELS FLORIDA HIGHWAYMEN PINK SUNSET: Daniels, Willie (1950-2021) Florida Highwaymen Painting. Oil on canvas - signed lower right. Executed in brush. In this luminous Florida river scene, the artist captures the quiet drama of dusk. A lon

Apr 25, 2026

WILLIE DANIELS FLORIDA HIGHWAYMEN PINK SUNSET

ISAAC KNIGHT FLORIDA HIGHWAYMEN POINCIANA BLOOM: Knight, "Issac" Isaac (1942-2022) Florida Highwaymen Painting. Oil on Canvas Board - signed lower right and verso. Executed in brush and palette knife. Knight’s circa-2002wetland scene centers o

Apr 25, 2026

ISAAC KNIGHT FLORIDA HIGHWAYMEN POINCIANA BLOOM

CHICO WHEELER FLORIDA HIGHWAYMEN DEER IN MOONLIGHT: Wheeler, Charles “Chico” (1946-2019) Florida Highwaymen Painting. Oil on Upson - signed lower right. Painted with brush and palette knife. The painting portrays a majestic buck surveying h

Apr 25, 2026

CHICO WHEELER FLORIDA HIGHWAYMEN DEER IN MOONLIGHT

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